9H-Fluoren-9-ol (9-Fluorenol; 9-Hydroxyfluorene) [C13H10O]

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141 reactions in Reaxys

2018-06-21 23h:17m:28s (UTC)

OH

1. Query

Search as: Product, As drawn, No mixtures ) AND (RX.PRO='9-fluorenol'))

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O

OH

Rx-ID: 164751 View in Reaxys 1/141 Yield 100 %

Conditions & References With hydrogen, 10 wt. % palladium on activated carbon in tetrahydrofuran, Time= 16h, T= 20 °C Hattori, Kazuyuki; Sajiki, Hironao; Hirota, Kosaku; Tetrahedron; vol. 57; nb. 23; (2001); p. 4817 - 4824 View in Reaxys

99 %

With sodium tetrahydroborate in tetrahydrofuran, water, Time= 0.2h, Heating Zeynizadeh, Behzad; Behyar, Tarifeh; Bulletin of the Chemical Society of Japan; vol. 78; nb. 2; (2005); p. 307 - 315 View in Reaxys

99 %

Stage 1: With sodium tetrahydroborate in methanol, T= 20 °C , Inert atmosphere, Cooling with ice Stage 2: With hydrogenchloride in methanol, water, pH= 7, Inert atmosphere Wang, Jing; Wan, Wen; Jiang, Haizhen; Gao, Yan; Jiang, Xueyin; Lin, Huaping; Zhao, Weiming; Hao, Jian; Organic Letters; vol. 12; nb. 17; (2010); p. 3874 - 3877 View in Reaxys

99 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 1h, T= 0 °C , Inert atmosphere George, Stephen R. D.; Elton, Timothy E.; Harper, Jason B.; Organic and Biomolecular Chemistry; vol. 13; nb. 43; (2015); p. 10745 - 10750 View in Reaxys

98 %

With sodium tetrahydroborate in tetrahydrofuran, Time= 1.5h, Heating, ultrasound irradiation Zeynizadeh, Behzad; Yahyaei, Saiedeh; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 59; nb.

6; (2004); p. 704 - 710 View in Reaxys

97.3 %

With Bacillus brevis in acetone, Time= 9h, T= 30 °C , varios reaction conditions, Product distribution Inoue, Tomomi; Tasaka, Tetsuya; Maruyama,Reiji; Sumita, Yasuteru; Ono, Shin; Inoue, Masami; Bioscience, Biotechnology, and Biochemistry; vol. 62; nb. 4; (1998); p. 814 - 815 View in Reaxys

97 %

With lithium aluminium tetrahydride in diethyl ether, Ambient temperature, other solvent: THF Brown, Eric; Leze, Antoine; Touet, Joel; Tetrahedron Letters; vol. 32; nb. 34; (1991); p. 4309 - 4310 View in Reaxys

97 %

With sodium tetrahydroborate, copper(II) exchange resin in ethanol, water, Time= 4h Sarkar; Rao; Ram; Synthetic Communications; vol. 23; nb. 3; (1993); p. 291 - 296 View in Reaxys

97.3 %

With Bacillus brevis in acetone, Time= 9h, T= 30 °C , pH 7.4 Inoue, Tomomi; Tasaka, Tetsuya; Maruyama,Reiji; Sumita, Yasuteru; Ono, Shin; Inoue, Masami; Bioscience, Biotechnology, and Biochemistry; vol. 62; nb. 4; (1998); p. 814 - 815 View in Reaxys

97 %

With sodium tetrahydroborate, TiO(acac)2 in tetrahydrofuran, Time= 0.15h, Heating Zeynizadeh, Behzad; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 58; nb. 12; (2003); p. 1220 - 1226 View in Reaxys

97 %

With sodium tetrahydroborate in water, Time= 0.0125h, microwave irradiation

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Zeynizadeh, Behzad; Setamdideh, Davood; Journal of the Chinese Chemical Society; vol. 52; nb. 6; (2005); p. 1179 - 1184 View in Reaxys 97 %

With sodium tetrahydroborate, pyrographite in tetrahydrofuran, water, Time= 0.166667h, T= 20 °C Setamdideh, Davood; Zeynizadeh, Behzad; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 10; (2006); p. 1275 - 1281 View in Reaxys

97 %

With sodium tetrahydroborate, ammonium oxalate in acetonitrile, Time= 1h, Reflux Setamdideh, Davood; Ghahremani, Sahar; South African Journal of Chemistry; vol. 65; (2012); p. 91 - 97 View in Reaxys

97 %

With hydrogen in tetrahydrofuran, Time= 48h, T= 60 °C , p= 760.051Torr Zhang, Guoqi; Scott, Brian L.; Hanson, Susan K.; Angewandte Chemie - International Edition; vol. 51; nb. 48; (2012); p.

12102 - 12106; Angew. Chem.; (2012); p. 12077 View in Reaxys

97 %

General procedure: In a typical experiment, complex 1 (6.1 mg, 10 tmol) and H[BAr’4].(Et2O)2 (10.1 mg, 10 tmol) were dissolved in THF (2.0 mE) in a 100 mE thick-walled glass vessel equipped with a TEFLON stopcock and a stir bar. The substrate (0.5 mmol) to be hydrogenated was then added. The vessel was degassed by freeze-pump-thaw and then hydrogen (1 or 4 atm) was added. The resulting solution was stirred at the desired temperature (25-60° C.) for the indicated reaction time. At the end of the reaction, the solvent was evaporated and the residue was passed through silica gel in a pipette. The solvent was removed under vacuum and the ‘H NMR spectrum of the crude product mixture was recorded in CDC13. Hydrogenation products were then isolated by column chromatography or preparative thin layer chromatography (“TLC”) using n-hexane/ethyl acetate (3:1, v/v) as an eluent. Isolated products were characterized by ‘H NMR and GCMS, with spectra matching those reported in the literature or authentic samples.

With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex, (bis[(2-dicyclohexylphosphino)ethyl]amine)cobalt(II)(CH2SiMe3), hydrogen in tetrahydrofuran, Time= 48h, T= 60 °C , p= 760.051Torr Patent; LOS ALAMOS NATIONAL SECURITY, LLC; Vasudevan, Kalyan V.; Zhang, Guoqi; Hanson, Susan K.; US2015/336862; (2015); (A1) English View in Reaxys

96.5 %

With potassium hydroxide, zinc in dimethyl sulfoxide, T= 30 °C Handoo, Kishan L.; Gadru, Kanchan; Tetrahedron Letters; vol. 27; nb. 12; (1986); p. 1371 - 1372 View in Reaxys

96 %

With silica gel, sodium cyanoborohydride, Time= 0.0277778h, Neat (no solvent), Microwave irradiation, regioselective reaction Kouhkan, Mehri; Zeynizadeh, Behzad; Bulletin of the Korean Chemical Society; vol. 31; nb. 10; (2010); p. 2961 - 2966 View in Reaxys

96 %

With zinc(II) tetrahydroborate in tetrahydrofuran, water, Time= 2h, T= 20 °C Setamdideh, Davood; Khezri, Behrooz; Rahmatollahzadeh, Mehdi; Poramjad, Avat Ali; Asian Journal of Chemistry; vol.

24; nb. 8; (2012); p. 3591 - 3596 View in Reaxys

96 %

2.4. Typical Procedure for the Reduction of Ketones withZn(BH4)2/2NaCl System in CH3CN General procedure: In a round-bottomed flask (10 mL), equipped with a magneticstirrer bar, a solution of acetophenone (0.121 g, l mmol) was prepared in CH3CN(3 mL). To this solution, Zn(BH4)2/2NaCl (0.210 g,1 mmol) was added. The resulting mixture was stirred at room temperature for 60 min. The reaction was monitored by TLC(eluent; Hexane/EtOAc: 10/1). After completion of the reaction, distilled water (5 mL) was added to the reaction mixture and stirred for 5 min. The mixture was extracted with CH2Cl2 (3 ×8 mL) and dried over anhydrous Na2SO4. Evaporation of the solvent followed column chromatography of the resulting crude material over silica gel (eluent; Hexane/EtOAc: 10/1) afforded crystals of 1-phenylethanol (0.l1 g, 93 percent yield,Table 2, entry 11).

With 2BH4 (1-)*Zn(2+)*Cl2Na2 in acetonitrile, Time= 1h, T= 20 °C Setamdideh, Davood; Khaledi, Leila; South African Journal of Chemistry; vol. 66; (2013); p. 150 - 157

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View in Reaxys 96 %

With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex, (bis[(2-dicyclohexylphosphino)ethyl]amine)cobalt(II)(CH2SiMe3), isopropyl alcohol in tetrahydrofuran, Time= 24h, T= 25 °C , Inert atmosphere, Glovebox, Schlenk technique, Sealed tube Zhang, Guoqi; Hanson, Susan K.; Chemical Communications; vol. 49; nb. 86; (2013); p. 10151 - 10153 View in Reaxys

95 %

With <Zn(BH4)2(dabco)> in tetrahydrofuran, Time= 2.3h, Heating Firouzabadi, Habib; Zeynizadeh, Behzad; Bulletin of the Chemical Society of Japan; vol. 70; nb. 1; (1997); p. 156 - 168 View in Reaxys

95 %

With methyltriphenylphosphonium tetrahydroborate, Time= 0.75h, T= 60 °C , Reduction Firouzabadi, Habib; Adibi, Mina; Phosphorus, Sulfur and Silicon and Related Elements; vol. 142; (1998); p. 125 - 147 View in Reaxys

95 %

With magnesium(II) perchlorate in methanol, acetonitrile, Time= 13h, Heating Li, Donghong; Zhang, Yongbin; Zhou, Guofu; Guo, Wei; Synlett; nb. 2; (2008); p. 225 - 228 View in Reaxys

95 %

With sodium tetrahydroborate, water, titanium(IV) oxide, Time= 0.0333333h, Microwave irradiation, regioselective reaction Setamdideh, Davood; Karimi, Zahra; Rahimi, Fatemeh; Oriental Journal of Chemistry; vol. 27; nb. 4; (2011); p. 1621 - 1634 View in Reaxys

95 %

Reduction of Benzaldehyde to Benzyl alcoholwith [Zn(BH4)2(2-MeOpy)] General procedure: A Typical ProcedureIn a round-bottomed flask (10 mL),equipped with a magnetic stirrer, a solution ofbanzaldehye (0.106 g, l mmol) in CH3CN (3 mL)was prepared. The complex reducing agent (0.1 g,0.5 mmol) was then added and the mixture wasstirred at room temperature. TLC monitored theprogress of the reaction (eluent; Hexane/EtOAc: 9/1). After completion of the reaction within 1 min, asolution of 5percent HCl (5 mL) was added to the reactionmixture and stirred for 5 min.

The mixture was extracted with CH2Cl2 (3 × 10 mL) and dried overthe anhydrous sodium sulfate. Evaporation of thesolvent and short column chromatography of theresulting crude material over silica gel (0.015-0.040mm) by eluent of (Hexane/EtOAc: 9/1) afforded thepure liquid benzyl alcohol (0.105 g, 98percent yield) With Zn(2+)*2BH4 (1-)*C6H7N in acetonitrile, Time= 3.5h, T= 20 °C , Reagent/catalyst, chemoselective reaction Khezri, Behrooz; Ghadimi, Farnaz Najaf; Karashi, Chonur Nevisandeh; Setamdideh, Davood; Oriental Journal of Chemistry; vol. 29; nb. 2; (2013); p. 623 - 629 View in Reaxys

95 %

A typical procedure for reduction of ketones with the NaBH4/(NH4)2SO4 system in wet-THF General procedure: In a round-bottomed flask (10 mL)equipped with a magnetic stirrer and a condenser,a solution of acetophenone (0.12 g, l mmol) in THF-H2O (3:0.6 mL) was prepared and NaBH4(0.038 g,1 mmol) and (NH4)2SO4(0.234 g, 2 mmol) wereadded and the mixture was stirred at roomtemperature for 90 minutes. TLC monitored theprogress of the reaction (Hexane/ EtOAc: 9/1). Aftercompletion of the reaction distilled water (5 mL)was added to the reaction mixture and it was stirredfor an additional 1 minute. The mixture wasextracted with CH2Cl2(3×10 mL) and dried overanhydrous sodium sulfate. Evaporation of thesolvent and short column chromatography of theresulting crude material over sil-ica gel (Hexane/EtOAc: 9/1) afforded the pure crystals of 1-phenylethanol (0.l1 g, 96percent yield, Table 1, entry 8).

With ammonium sulfate, sodium tetrahydroborate in tetrahydrofuran, water, Time= 2h, T= 20 °C Akbarzadeh, Saber; Setamdideh, Davood; Hedayati, Mohammad Alizadeh; Oriental Journal of Chemistry; vol. 30; nb. 4; (2014); p. 1989 - 1992 View in Reaxys

95 %

With C8H18B2N4O2Zn in acetonitrile, Time= 1.5h, Reflux Abdollahpour, Fatemeh; Setamdideh, Davood; Oriental Journal of Chemistry; vol. 31; nb. 3; (2015); p. 1787 - 1792 View in Reaxys

94 %

With Zn(BH4)2(bpy) in acetonitrile, Time= 1.5h, T= 20 °C

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Zeynizadeh, Behzad; Bulletin of the Chemical Society of Japan; vol. 76; nb. 2; (2003); p. 317 - 326 View in Reaxys 94 %

With sodium tetrahydroborate, Dowex1-x8 in tetrahydrofuran, Time= 1.8h, Heating Zeynizadeh, Behzad; Shirini, Farhad; Journal of Chemical Research - Part S; nb. 6; (2003); p. 335 - 339 View in Reaxys

94 %

With sodium tetrahydroborate, sodium hydrogen sulfate in acetonitrile, Time= 0.3h, T= 20 °C Zeynizadeh, Behzad; Behyar, Tarifen; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 60; nb. 4; (2005); p. 453 - 457 View in Reaxys

93 %

With polymeric xylylene-ionene borohydride in isopropyl alcohol, Time= 2.7h, Heating Lakouraj, Moslem M.; Tajbakhsh, Mahmood; Mahalli, Majid S.; Monatshefte fur Chemie; vol. 139; nb. 2; (2008); p. 117 123 View in Reaxys

93 %

A typical procedure for reduction of ketones to alcohols with the Zn(BH4)2/Al2O3 system in THF General procedure: In a round-bottomed flask (10 mL) equipped with a magnetic stirrer, a solution ofacetophenone (0.121 g, 1 mmol) in THF (3 mL) was prepared. To this solution, Zn(BH4)2(0.095 g, 1 mmol) and then neutral Al2O3 (0.101 g, 1 mmol) were added. The resulting mixturewas stirred at room temperature for 60 min. The progress of the reaction was monitoredby TLC (eluent, CCl4/Et2O: 5/2). After completion of the reaction, distilled water (1 mL) wasadded to the reaction mixture and then stirring was continued for an additional 5 min. Themixture was extracted with CH2Cl2 (3×8 mL) and dried over anhydrous sodium sulfate. Evaporationof the solvent and short column chromatography of the resulting crude material overabove mentioned silica gel afforded pure crystals of 1-phenylethanol (0.11 g, 93 percent yield,Table IV, entry 2) With aluminum oxide, zinc(II) tetrahydroborate in tetrahydrofuran, Time= 1.6h, T= 20 °C , chemoselective reaction Setamdideh, Davood; Khezri, Behrooz; Rahmatollahzadeh, Mehdi; Journal of the Serbian Chemical Society; vol. 78; nb. 1; (2013); p. 1 - 13 View in Reaxys

93 %

With sodium tetrahydroborate in tetrahydrofuran, Time= 1.25h, T= 20 °C , Reagent/catalyst Setamdideh, Davood; Karimi, Zahra; Alipouramjad, Avat; Journal of the Chinese Chemical Society; vol. 60; nb. 6; (2013); p. 590 - 596 View in Reaxys

92 %

With polydibenzo-18-crown-6-borohydride in ethanol, Time= 26h, T= 40 - 50 °C Sarkar; Rao, Br; Tetrahedron Letters; vol. 32; nb. 19; (1991); p. 2157 - 2160 View in Reaxys

91 %

Reduction of Acetophenone to 1-phenylethanolwith [Zn(BH4)2(acr)], A Typical Procedure General procedure: In a round-bottomed flask (10 mL),equipped with a magnetic stirrer, a solution ofacetophenone (0.120 g, 1mmol) in CH3CN (3 mL)was prepared. The complex reducing agent (0.274g, 1mmol) was then added as a solid and the mixturewas stirred at reflux conditions. TLC monitored theprogress of the reaction (eluent; CCl4/Et2O : 5/2). After completion of the reaction in 90 min, a solutionof 5percent HCl (5 mL) was added to the reaction mixtureand stirred for 10 min. The mixture was extractedwith CH2Cl2(3 × 10 mL) and dried over theanhydrous sodium sulfate. Evaporation of thesolvent and short column chromatography of theresulting crude material over silica gel by eluent ofCCl4/Et2O : 5/2 afforded the pure liquid benzylalcohol (0.113 g, 93percent yield).

With [Zn(tetrahydroborato)2(acridine)] in acetonitrile, Time= 2h, Reflux Mohammadi, Sina; Setamdideh, Davood; Oriental Journal of Chemistry; vol. 31; nb. 4; (2015); p. 2395 - 2399 View in Reaxys

90 %

With chromium(II) diacetate dimer in N,N-dimethyl-formamide, Time= 3h, T= 90 °C Fournier, F.; Berthelot, J.; Pascal, Y. L.; Tetrahedron; vol. 40; nb. 2; (1984); p. 339 - 347 View in Reaxys

90 %

With methanol, potassium hydroxide, aluminium, Time= 0.25h, Ambient temperature

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Khurana, Jitender M.; Sehgal, Arti; Gogia, Amita; Manian, Aparna; Maikap, Golak C.; Journal of the Chemical Society Perkin Transactions 1; nb. 17; (1996); p. 2213 - 2215 View in Reaxys 90 %

With Zn(BH4)2(Ph3P)2, Time= 4h, Reduction Firouzabadi, Habib; Adibi, Mina; Ghadami, Mahboobeh; Phosphorus, Sulfur and Silicon and Related Elements; vol. 142; (1998); p. 191 - 220 View in Reaxys

90 %

Typical procedure for the reduction of carbonylcompounds with Zn(BH4)2 under ultrasonicirradiation in CH3CN General procedure: In a round-bottomed flask (10 mL) equipped with a magnetic stirrer bar, a solution of benzaldehyde (0.1061 g, l mmol) was prepared inCH3CN (3 mL). To this solution Zn(BH4)2 (0.095 g,1mmol) was added. The resulting mixture was stirredunder ultrasonic waves at room temperature for 5min. The progress of the reduction reaction wasmonitored by TLC (eluent:CCl4/Et2O:5/2). Aftercompletion of the reaction, distilled water (5 mL)was added to the reaction mixture and stirred for 5min. The mixture was extracted with CH2Cl2 (3×10mL) and dried over anhydrous Na2SO4. Evaporationof the solvent afforded pure benzyl alcohol (0.102g, 95percent yield).

With zinc(II) tetrahydroborate in acetonitrile, Time= 2h, T= 20 °C , Sonication Fanari, Siamak; Setamdideh, Davood; Oriental Journal of Chemistry; vol. 30; nb. 2; (2014); p. 695 - 697; View in Reaxys

88 %

With Montmorillonite, (-)N-dodecyl-N-methyl ephedrinium borohydride in benzene, Time= 15h Sarkar; Rao; Tetrahedron Letters; vol. 32; nb. 9; (1991); p. 1247 - 1250 View in Reaxys

86 %

With hydrogen, 10 wt. % palladium on activated carbon, ethylenediamine in methanol, Time= 24h Sajiki, Hironao; Hattori, Kazuyuki; Hirota, Kosaku; Journal of the Chemical Society - Perkin Transactions 1; nb. 24; (1998); p. 4043 - 4044 View in Reaxys

85 %

Stage 1: With cyclopentadienyl iron(II) dicarbonyl dimer, diethoxymethylane, Time= 24h, T= 100 °C Stage 2: With water, sodium hydroxide in methanol Jung, Thais Cordeiro; Argouarch, Gilles; Van De Weghe, Pierre; Catalysis Communications; vol. 78; (2016); p. 52 - 54 View in Reaxys

84 %

With lithium vanadium(I) dihydride in tetrahydrofuran, Time= 12h, T= 25 °C , Inert atmosphere Eisch, John J.; Fregene, Paul O.; European Journal of Organic Chemistry; nb. 26; (2008); p. 4482 - 4492 View in Reaxys

83 %

With trans-RuCl(2-(2-pyridyl-6-ol)-1,10-phenanthroline)(PPh3)2PF6, potassium tert-butylate, isopropyl alcohol, Time= 0.75h, T= 80 °C , Inert atmosphere, Schlenk technique, Time Paul, Bhaskar; Chakrabarti, Kaushik; Kundu, Sabuj; Dalton Transactions; vol. 45; nb. 27; (2016); p. 11162 - 11171 View in Reaxys

75 %

With benzaldehyde, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4-dimethyl-1,2,4-triazolium iodide in ethanol, Time= 24h, T= 23 °C Chan, Audrey; Scheidt, Karl A.; Journal of the American Chemical Society; vol. 128; nb. 14; (2006); p. 4558 - 4559 View in Reaxys

73 %

in acetone, Time= 72h, Actinomyces roseochromogenes-522 cells Davidenko, T. I.; Sevast'yanova, E. V.; Pharmaceutical Chemistry Journal; vol. 14; nb. 7; (1980); p. 463 - 465; Khimiko-Farmatsevticheskii Zhurnal; vol. 14; nb. 7; (1980); p. 66 - 68 View in Reaxys

66 %

With isopropyl alcohol, Time= 1.5h, T= 300 °C Sominsky, Lena; Rozental, Esther; Gottlieb, Hugo; Gedanken, Aharon; Hoz, Shmaryahu; Journal of Organic Chemistry; vol. 69; nb. 5; (2004); p. 1492 - 1496

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View in Reaxys 65 %

With water, 1,8-diazabicyclo[5.4.0]undec-7-ene, bis(pinacol)diborane, Time= 10h, T= 60 °C , Sealed tube, chemoselective reaction Xuan, Qingqing; Zhao, Cong; Song, Qiuling; Organic and Biomolecular Chemistry; vol. 15; nb. 24; (2017); p. 5140 - 5144 View in Reaxys

48 %

With Quinoline N-oxide, n-butyllithium in tetrahydrofuran, hexane, Time= 1h, T= -30 - 25 °C , Reduction Tagawa, Yoshinobu; Nomura, Manami; Yamashita, Hiroyuki; Goto, Yoshinobu; Hamana, Masatomo; Heterocycles; vol.

51; nb. 10; (1999); p. 2385 - 2397 View in Reaxys in n-heptane, T= 19.9 °C , Irradiation, other solvent: ethanol, Product distribution, Quantum yield Kudryasheva, N. S.; Val'kova, G. A.; Shigorin, D. N.; Gorelik, M. V.; Russian Journal of Physical Chemistry; vol. 63; nb. 1; (1989); p. 91 - 94; Zhurnal Fizicheskoi Khimii; vol. 63; (1989); p. 177 - 182 View in Reaxys With potassium hydroxide, nickel, Hydrogenation Forrest; Tucker; Journal of the Chemical Society; (1948); p. 1137,1140 View in Reaxys With potassium hydroxide Huntress; Seikel; Journal of the American Chemical Society; vol. 61; (1939); p. 816,819 View in Reaxys With diethyl ether, ethanol, benzene, weiteres Reagens: Natrium-Amalgam Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 770,773 View in Reaxys With sodium isopropylate, isopropyl alcohol Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 391,394 View in Reaxys With aluminum isopropoxide, T= 150 °C Macbeth; Mills; Journal of the Chemical Society; (1949); p. 2646,2648 View in Reaxys With aluminum tri-sec-butoxide, T= 150 °C Macbeth; Mills; Journal of the Chemical Society; (1949); p. 2646,2648 View in Reaxys With sodium amalgam, ethanol Barbier; Chemische Berichte; vol. 7; (1874); p. 1649; Chemische Berichte; vol. 8; (1875); p. 829 View in Reaxys Barbier; Annales de Chimie (Cachan, France); vol. <5> 7; (1876); p. 510; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1876); p. 418 View in Reaxys With potassium hydroxide, ethanol, zinc Werner; Grob; Chemische Berichte; vol. 37; (1904); p. 2895 View in Reaxys With ammonium hydroxide, ethanol, zinc Werner; Grob; Chemische Berichte; vol. 37; (1904); p. 2895 View in Reaxys

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With acetic acid, zinc Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys With acetic acid, zinc Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys Kliegl; Chemische Berichte; vol. 62; (1929); p. 1330; Chemische Berichte; vol. 64; (1931); p. 2422 View in Reaxys With diethyl ether, aluminium amalgam Sieglitz; Jassoy; Chemische Berichte; vol. 55; (1922); p. 2039 View in Reaxys With sodium tetrahydroborate Pan; Fletcher; Journal of Organic Chemistry; vol. 23; (1958); p. 799,800; Journal of Organic Chemistry; vol. 27; (1962); p.

3639,3640 View in Reaxys Ohashi, Mamoru; Furukawa, Yuji; Tsujimoto, Kazuo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 2613 - 2616 View in Reaxys Ulagi; Kuselan; Karunakaran; Monatshefte fur Chemie; vol. 132; nb. 7; (2001); p. 799 - 804 View in Reaxys Ram, Ram N; Meher, Nabin Kumar; Tetrahedron; vol. 58; nb. 15; (2002); p. 2997 - 3001 View in Reaxys With ethanol, aluminium amalgam Cohen; Recueil des Travaux Chimiques des Pays-Bas; vol. 38; (1919); p. 121 View in Reaxys With ethanol, sodium acetate, Electrolysis Arai; ; nb. 9; (1959); p. 7,9; ; (1960); p. 24028 View in Reaxys With kieselguhr, ethanol, nickel, T= 70 - 75 °C , p= 84583.4Torr , Hydrogenation Hurd; Mold; Journal of Organic Chemistry; vol. 13; (1948); p. 339,342 View in Reaxys With aluminum isopropoxide, isopropyl alcohol Lund; Chemische Berichte; vol. 70; (1937); p. 1520,1524 View in Reaxys Baker; Adkins; Journal of the American Chemical Society; vol. 62; (1940); p. 3305,3306 View in Reaxys With lithium aluminium tetrahydride, diethyl ether, T= 35 °C Hochstein; Journal of the American Chemical Society; vol. 71; (1949); p. 305 View in Reaxys With aluminum tri-sec-butoxide, iso-butanol Ferrier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 220; (1945); p. 460 View in Reaxys With potassium hydroxide, 10 wt. % palladium on activated carbon, Hydrogenation Forrest; Tucker; Journal of the Chemical Society; (1948); p. 1137,1140 View in Reaxys

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in n-heptane, T= 293 °C , Irradiation, other solvent: ethanol Kudryasheva, N. S.; Val'kova, G. A.; Shigorin, D. N.; Gorelik, M. V.; Russian Journal of Physical Chemistry; vol. 63; nb. 1; (1989); p. 91 - 94; Zhurnal Fizicheskoi Khimii; vol. 63; (1989); p. 177 - 182 View in Reaxys With sodium tetrahydroborate in methanol Krogh, Erik; Wan, Peter; Tetrahedron Letters; vol. 27; nb. 7; (1986); p. 823 - 826 View in Reaxys Grasse; Brauer; Zupancic; Kaufmann; Schuster; Journal of the American Chemical Society; vol. 105; nb. 23; (1983); p.

6833 - 6845 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, Time= 1h, Heating, k, Yield given Bilger, Christine; Royer, Rene; Demerseman, Pierre; Synthesis; nb. 11; (1988); p. 902 - 904 View in Reaxys With water, sodium, 1.) 1,2-dimethoxyethane, -10 deg C, 5 d, Multistep reaction Hirayama, Masatoshi; Suzuki, Hideto; Ohhata, Hiroshi; Chemistry Letters; (1987); p. 413 - 416 View in Reaxys With methanol, 9,10-dihydro-10-methylacridine in benzene, Irradiation Peters, Kevin S.; Pang, Edward; Rudzki, Jeanne; Journal of the American Chemical Society; vol. 104; nb. 20; (1982); p. 5535 - 5537 View in Reaxys With methanol, methyltriphenylphosphonium tetrahydroborate, 1) CH2Cl2, reflux, 18 h, 2) 2 h, Yield given. Multistep reaction Firouazabadi; Adibi; Synthetic Communications; vol. 26; nb. 13; (1996); p. 2429 - 2441 View in Reaxys With sodium tetrahydroborate in tetrahydrofuran, methanol, T= 0 - 20 °C Ulmschneider, Sarah; Mueller-Vieira, Ursula; Klein, Christian D.; Antes, Iris; Lengauer, Thomas; Hartmann, Rolf W.; Journal of Medicinal Chemistry; vol. 48; nb. 5; (2005); p. 1563 - 1575 View in Reaxys Stage 1: With [MCM-41]-Sm[N(SiHMe2)2]x(THF)y in hexane, Time= 20h, T= 20 °C , Reduction Stage 2: With hydrogenchloride in hexane, Hydrolysis, Further stages.

Nagl, Iris; Widenmeyer, Markus; Grasser, Stefan; Koehler, Klaus; Anwander, Reiner; Journal of the American Chemical Society; vol. 122; nb. 7; (2000); p. 1544 - 1545 View in Reaxys 100 % Spectr.

With sodium hydroxide, titanium(III) chloride in methanol, Time= 0.0833333h, T= 20 - 25 °C , pH= 10 - 11 Clerici, Angelo; Pastori, Nadia; Porta, Ombretta; European Journal of Organic Chemistry; nb. 19; (2002); p. 3326 - 3335 View in Reaxys

92 % Chromat.

With potassium tert-butylate, hydrogen, RuCl2(PPh3)(Me4BPPy) in isopropyl alcohol, Time= 4h, T= 25 °C , p= 15201Torr Yu; Zeng; Sun; Deng; Dong; Chen; Wang; Pei; Journal of Organometallic Chemistry; vol. 692; nb. 11; (2007); p. 2306 - 2313 View in Reaxys

79 %Chromat.

With ruthenium tris(2,2,6,6-tetramethyl-3,5-heptanedionate), hydrogen in tetrahydrofuran, Time= 6h, T= 80 °C , p= 20686.5Torr Bhor, Malhari D.; Panda, Anil G.; Nandurkar, Nitin S.; Bhanage, Bhalchandra M.; Tetrahedron Letters; vol. 49; nb. 45; (2008); p. 6475 - 6479 View in Reaxys

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81 %Chromat.

With ethanol, titanium(IV) oxide, Time= 2h, T= 32 °C , Inert atmosphere, UV-irradiation Kohtani, Shigeru; Yoshioka, Eito; Saito, Kenji; Kudo, Akihiko; Miyabe, Hideto; Catalysis Communications; vol. 11; nb. 13; (2010); p. 1049 - 1053 View in Reaxys 5.4. Reactions of ketones and aldehydes with AB in methanol General procedure: A 0.5 mm NMR tube was charged with ketone or aldehyde (0.2 mmol), AB (0.1 mmol), and deuterated methanol. The tube was covered with a plastic cap and inserted into the NMR machine after shaking. The reaction courses were monitored by 1H and 11B NMR every several minutes (depending on the reaction rates). The typical resonances of the starting materials gradually decreased while new signals of the saturated products appeared. After the ketone or aldehyde disappeared completely in the 1H NMR spectrum, 13C NMR spectrum was recorded. For a large scale reaction in normal methanol, the solvent and all volatile compounds (trimethyl borate and ammonia) were removed by high vacuum after the reaction, and the remaining alcohol was pure to the limit of the NMR with nearly 100percent yield.

With methanol, ammonia–borane, T= 20 °C , Inert atmosphere Yang, Xianghua; Fox, Thomas; Berke, Heinz; Tetrahedron; vol. 67; nb. 37; (2011); p. 7121 - 7127 View in Reaxys Reaction Steps: 2 1: [HC{(Me)CN(2,6-iPr2C6H3)}2MgnBu] / benzene-d6 / 3 h / 20 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride; water / methanol; toluene / 1 h / Reflux; Inert atmosphere With hydrogenchloride, [HC{(Me)CN(2,6-iPr2C6H3)}2MgnBu], water in methanol, benzene-d6, toluene Arrowsmith, Merle; Hadlington, Terrance J.; Hill, Michael S.; Kociok-Koehn, Gabriele; Chemical Communications; vol.

48; nb. 38; (2012); p. 4567 - 4569 View in Reaxys

> 99 %Chromat.

With chloro(η6-p-cymene)(η2C,N-3-methyl-1-(2-picolyl)imidazol-2-ylidene)ruthenium(II) hexafluorophosphate, isopropyl alcohol, potassium hydroxide, Time= 15h, T= 82 °C , Inert atmosphere, Schlenk technique, Mechanism, Reagent/catalyst Fernandez, Francys E.; Puerta, M. Carmen; Valerga, Pedro; Organometallics; vol. 31; nb. 19; (2012); p. 6868 - 6879 View in Reaxys With [{(CH3)2C3HN2-C5H3N-C3H3N2}RuCl2(PPh3)], potassium isopropoxide, isopropyl alcohol, Time= 0.00277778h, T= 82 °C , Inert atmosphere Jin, Weiwei; Wang, Liandi; Yu, Zhengkun; Organometallics; vol. 31; nb. 15; (2012); p. 5664 - 5667,4 View in Reaxys Typical procedure for transfer hydrogenation of ketones General procedure: In an oven-dried round bottom flask, were placed ketone (2.4 mmol), catalyst (3 mol), base (12 mol), internal standard (m-xylene, 30 L, 0.24 mmol) and i-PrOH (5 mL) at room temperature. The reaction mixture was heated at 82 °C for the required reaction time under an atmosphere of nitrogen. Aliquots (0.2 mL) were taken at fixed time and the catalyst removed as precipitate from the reaction mixture by the addition of diethyl ether. The organic layer was neutralized with 1 N HCl, washed with water and dried over anhydrous Na2SO4. The combined organic layer passed through a short path of silica gel and then subjected to GCMS analysis. The conversions obtained are related to the residual unreacted ketone and are averages of two runs in the case of all catalytic reactions.

With C55H41ClN2O3P2Ru, isopropyl alcohol, potassium hydroxide in m-xylene, Time= 4h, T= 20 - 82 °C , Inert atmosphere Prabhu, Rupesh Narayana; Ramesh, Rengan; Journal of Organometallic Chemistry; vol. 718; (2012); p. 43 - 51,9 View in Reaxys Reaction Steps: 2 1: mesoporous silica-supported zirconium amide complex / benzene-d6 / 2 h / 60 °C / Inert atmosphere 2: sodium hydroxide / water / Inert atmosphere With sodium hydroxide in benzene-d6, water Eedugurala, Naresh; Wang, Zhuoran; Chaudhary, Umesh; Nelson, Nicholas; Kandel, Kapil; Kobayashi, Takeshi; Slowing, Igor I.; Pruski, Marek; Sadow, Aaron D.; ACS Catalysis; vol. 5; nb. 12; (2015); p. 7399 - 7414 View in Reaxys

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Syntheses of 1c-f, 1h-k, and 1q General procedure: To a solution of the corresponding ketone in methanol (0.60 M) was added sodiumborohydride (0.33 equiv.) and the resulting mixture was stirred for 2 h at 0 °C. Afterstirring, additional sodium borohydride (0.33 equiv.) was added to the mixture tocomplete the transformation. After 2 h, water was added to quench the reaction, andthe mixture was extracted with diethyl ether (3 times). The extracts were dried overanhydrous MgSO4, filtered, and concentrated under reduced pressure. The residuewas chromatographed on silica gel to afford desired alcohol.

With sodium tetrahydroborate in methanol, Time= 4h, T= 0 °C Komagawa, Hiromi; Maejima, Yukako; Nagano, Takashi; Synlett; vol. 27; nb. 5; (2016); p. 789 - 793 View in Reaxys 1 :(0.1 mol) was dissolved in THF, 7.57 g (0.2 mol) of sodium borohydride was added and the reaction was refluxed for 4 hours.

The solvent was evaporated to dryness, extracted with water, extracted with methylene chloride, washed three times with water, Sodium drying overnight, filtered out of sodium sulfate, recovery of dichloromethane, a white solid. The white solid was suspended in benzene 500 ml, and 47.59 g of thionyl chloride was added dropwise to the ice bath. After the dropwise addition, the mixture was allowed to warm to room temperature. The reaction was stirred overnight and the solvent was evaporated to dryness to give 12 g of white solid, mp 87-89 ° C Rate of 60percent.

With sodium tetrahydroborate in tetrahydrofuran, Time= 4h, Reflux Patent; The Chinese People's Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Yun Liuhong; Dong Guoxing; Zhang Shuzhuo; Zhang Cheng; Wu Ning; Wang Haoshan; Pang Chong; Chen Ying; Wang Bo; Liu Ying; Liu Xiaoyan; Su Ruibin; Yang Rifang; Zheng Jianquan; Li Jin; (50 pag.); CN103130745; (2017); (B) Chinese View in Reaxys Screening of substrates General procedure: A general procedure was applied depending on the physical state of the substrate, as follows: a. For solid ketones: The catalyst (3, 9µmol) and the ketone (1.85mmol) were added to a Schlenk flask. Air was purged by three vacuum/gas (N2) cycles. Degassed iPrOH (3.3mL) was added, followed by base from a freshly prepared stock solution of KOH in iPrOH (90µmol, 200µL from stock solution 0.45mol/L). A reflux condenser was connected to the Schlenk and the system was heated to 80°C in an oil bath. After the reaction time (24h) the heating was stopped and the yield was determined by 1H NMR. b. For liquid ketones: The catalyst (3, 9µmol) was added to a Schlenk flask. Air was purged by three vacuum/gas (N2) cycles. Then, the ketone (1.85mmol), iPrOH (3.3mL), and KOH (90µmol, 200µL from stock iPrOH solution 0.45mol/L) were added with a syringe. A reflux condenser was connected to the Schlenk and the system was heated to 80°C in an oil bath. After the reaction time (24h) the heating was stopped and the yield was determined by 1H NMR With C50H54IrO3P2 (1+)*F6P(1-), isopropyl alcohol, potassium hydroxide, Time= 24h, T= 80 °C , Schlenk technique, Inert atmosphere Landaeta, Vanessa R.; Rosa, Abel D. Salazar-La; Rodríguez-Lugo, Rafael E.; Inorganica Chimica Acta; vol. 470; (2018); p.

303 - 311 View in Reaxys 83 %Chromat.

2.3. General procedure for TH of ketones catalyzed by 3 General procedure: Under a nitrogen atmosphere, a mixture of ketone (2 mmol),catalyst 3 (0.01 mmol), and 2-propanol (18 mL) was stirred at 82 °C for 10 min. Then, iPrOK solution in 2-propanol (2.0 mL,0.1 mol/L, 0.2 mmol) was introduced to initiate the reaction.The reaction mixture was stirred at reflux. After the statedtime, 0.1 mL of the reaction mixture was sampled and immediatelydiluted with 0.5 mL of 2-propanol precooled to 0 °C, andfiltered through a short pad of celite to quench the reaction byremoving the complex catalyst. The resultant filtrate was usedfor GC analysis. After the reaction was finished, the mixture wascondensed under reduced pressure and subjected to flash silicagel column chromatography to afford the alcohol product. The alcohol products were identified by comparison with authenticsamples using NMR and GC analyses.

Stage 1: With C49H44Cl2N9P2Ru(1+)*Cl(1-), isopropyl alcohol, Time= 0.166667h, T= 82 °C , Inert atmosphere, Schlenk technique Stage 2: With potassium isopropoxide, isopropyl alcohol, Time= 0.5h, Reflux, Inert atmosphere, Schlenk technique Wang, Liandi; Liu, Tingting; Chinese Journal of Catalysis; vol. 39; nb. 2; (2018); p. 327 - 333 View in Reaxys With sodium tetrahydroborate in methanol, Time= 4h, T= 0 - 20 °C

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Suresh, Amaroju; Srinivasarao, Singireddi; Agnieszka, Napiórkowska; Ewa, Augustynowicz-Kopeć; Alvala, Mallika; Lherbet, Christian; Chandra Sekhar, Kondapalli Venkata Gowri; Chemical Biology and Drug Design; vol. 91; nb. 6; (2018); p. 1078 - 1086 View in Reaxys OH

Rx-ID: 1767541 View in Reaxys 2/141 Yield 48 %

Conditions & References With tert.-butylhydroperoxide, tungsten(VI) oxide in water, Time= 12h, T= 80 °C Shaikh, Tanveer Mahammad Ali; Sudalai, Arumugam; European Journal of Organic Chemistry; nb. 29; (2008); p. 4877 4880 View in Reaxys

40 %

in acetone, Time= 48h, Actinomyces roseochromogenes-522 cells Davidenko, T. I.; Sevast'yanova, E. V.; Pharmaceutical Chemistry Journal; vol. 14; nb. 7; (1980); p. 463 - 465; Khimiko-Farmatsevticheskii Zhurnal; vol. 14; nb. 7; (1980); p. 66 - 68 View in Reaxys With 4-tert-butylpyridine, (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride, tetraphenylphosphonium monoperoxysulfate in 1,2-dichloro-ethane, T= 30 °C , Rate constant, Product distribution Bolzonella, Eva; Campestrini, Sandro; Di Furia, Fulvio; Ghiotti, Patrizia; Journal of Physical Organic Chemistry; vol. 9; nb. 8; (1996); p. 539 - 544 View in Reaxys Yield given. Multistep reaction Harvey, Ronald G.; Abu-shqara, Elias; Yang, ChengXi; Journal of Organic Chemistry; vol. 57; nb. 23; (1992); p. 6313 - 6317 View in Reaxys Reaction Steps: 2 1: 21 percent / 6M tert.butyl hydroperoxide / 0.2M 2,4-dimethylpentane-2,4-diol cyclic chromate / CH2Cl2; CCl4 / 8 h / 0 °C 2: LiAlH4 With tert.-butylhydroperoxide, lithium aluminium tetrahydride, 2,4-dimethylpentane-2,4-diol cyclic chromate in tetrachloromethane, dichloromethane Muzart, Jacques; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3139 - 3142 View in Reaxys Reaction Steps: 2 1: tetrachloromethane 2: aqueous acetic acid With tetrachloromethane, acetic acid Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371 View in Reaxys Reaction Steps: 2 1: tetrachloromethane 2: sodium acetate; aqueous acetic acid With tetrachloromethane, sodium acetate, acetic acid Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371 View in Reaxys Reaction Steps: 2 1: carbon disulfide; bromine / Einwirkung von Sonnenlicht oder UV-Licht 2: aqueous acetic acid

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With carbon disulfide, bromine, acetic acid Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371 View in Reaxys Reaction Steps: 2 1: carbon disulfide; bromine / Einwirkung von Sonnenlicht oder UV-Licht 2: sodium acetate; aqueous acetic acid With carbon disulfide, bromine, sodium acetate, acetic acid Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371 View in Reaxys Reaction Steps: 2 1: tetrachloromethane 2: aqueous acetic acid With tetrachloromethane, acetic acid Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371 View in Reaxys Reaction Steps: 2 1: tetrachloromethane 2: sodium acetate; aqueous acetic acid With tetrachloromethane, sodium acetate, acetic acid Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371 View in Reaxys With NADPH, Enzymatic reaction Whitehouse, Christopher J. C.; Yang, Wen; Yorke, Jake A.; Rowlatt, Benjamin C.; Strong, Anthony J. F.; Blanford, Christopher F.; Bell, Stephen G.; Bartlam, Mark; Wong, Luet-Lok; Rao, Zihe; ChemBioChem; vol. 11; nb. 18; (2010); p.

2549 - 2556 View in Reaxys With C29H23Cl2FeN7O2 (1+)*Cl(1-), dihydrogen peroxide in acetonitrile, Time= 48h, T= 40 °C , Catalytic behavior, Time Tyagi, Nidhi; Singh, Ovender; Ghosh, Kaushik; Catalysis Communications; vol. 95; (2017); p. 83 - 87 View in Reaxys With potassium phosphate, cytochrome P450 monooxygenases from Thermobispora bispora, NADPH in dimethyl sulfoxide, pH= 8, Enzymatic reaction, Reagent/catalyst Tavanti, Michele; Porter, Joanne L.; Sabatini, Selina; Turner, Nicholas J.; Flitsch, Sabine L.; ChemCatChem; vol. 10; nb.

5; (2018); p. 1042 - 1051 View in Reaxys O

OH

Rx-ID: 1767539 View in Reaxys 3/141 Yield 88.7 %, 11.3 %

Conditions & References With N -hydroxyphthalimide, oxygen, butane-2,3-dione dioxime in acetonitrile, Time= 10h, T= 80 °C , p= 3750.38Torr Zheng, Gengxiu; Liu, Chunhong; Wang, Qiufen; Wang, Mingyu; Yang, Guanyu; Advanced Synthesis and Catalysis; vol.

351; nb. 16; (2009); p. 2638 - 2642 View in Reaxys

63 %, 11 %

With sodium percarbonate, adogen 464, bis-(tributyltin oxide) dioxochromium(VI), toluene-4-sulfonic acid in acetonitrile, Time= 20h, Heating

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Muzart, Jacques; Aiet-Mohand, Samia; Tetrahedron Letters; vol. 36; nb. 32; (1995); p. 5735 - 5736 View in Reaxys 50 %

With cerium(III) sulfate, barium bromate in water, acetonitrile, Time= 24h, Heating, Title compound not separated from byproducts Shaabani, Ahmad; Lee, Donald G.; Synthetic Communications; vol. 33; nb. 11; (2003); p. 1845 - 1854 View in Reaxys

45 %, 24 %

With N -hydroxyphthalimide, oxygen in ethyl acetate, Time= 10h, T= 70 °C , p= 760.051Torr , Catalytic behavior Rezaeifard, Abdolreza; Khoshyan, Ashkan; Jafarpour, Maasoumeh; Pourtahmasb, Mehrdad; RSC Advances; vol. 7; nb.

26; (2017); p. 15754 - 15761 View in Reaxys

12 % Chromat., 21 %

With <(n-C4H9)4N>5PZnMo2W9O39*3H2O, dihydrogen peroxide in chloroform, Time= 24h, Title compound not separated from byproducts Tangestaninejad, Shahram; Yadollahi, Bahram; Chemistry Letters; nb. 6; (1998); p. 511 - 512 View in Reaxys

12 %, 21 % Chromat.

With <(n-C4H9)4N>5PZnMo2W9O39*3H2O, dihydrogen peroxide in chloroform, Time= 24h, Title compound not separated from byproducts Tangestaninejad, Shahram; Yadollahi, Bahram; Chemistry Letters; nb. 6; (1998); p. 511 - 512 View in Reaxys With oxygen, potassium hydride in tetrahydrofuran, Time= 0.0833333h, T= 20 °C , other alkali-metal hydrides; various aprotic solvents; different time, Product distribution Grigoryan, G. S.; Tovmasyan, V. S.; Malkhasyan, A. Ts.; Martirosyan, G. T.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 5.2; (1989); p. 932 - 935; Zhurnal Organicheskoi Khimii; vol. 25; nb. 5; (1989); p.

1036 - 1039 View in Reaxys With sodium hydroxide, sodium tetrahydroborate, oxygen, 18-crown-6 ether in dimethyl sulfoxide, Time= 0.3h, further base, further solvents; influence of solvent polarity, base strength, use of crown ether, Product distribution Grigoryan, G. S.; Tovmasyan, V. S.; Malkhasyan, A. Ts.; Martirosyan, G. T.; Beletskaya, I. P.; Doklady Chemistry; vol.

295; nb. 8; (1987); p. 353 - 356; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 295; nb. 5; (1987); p. 1124 - 1127 View in Reaxys Stage 1: With triethylsilane, [Bu4N]4W10O32, oxygen in acetonitrile, Time= 1h, T= 5 - 10 °C , Irradiation Stage 2: With triphenylphosphine, Further stages.

Lykakis, Ioannis N.; Orfanopoulos, Michael; Tetrahedron Letters; vol. 45; nb. 41; (2004); p. 7645 - 7649 View in Reaxys Stage 1: With N -hydroxyphthalimide, xanth-9-one, oxygen, tetramethlyammonium chloride in acetonitrile, Time= 4h, T= 60 °C , p= 3750.38Torr , Autoclave Stage 2: With triphenylphosphine in acetonitrile, Time= 0.5h, T= 20 °C Du, Zhongtian; Sun, Zhiqiang; Zhang, Wei; Miao, Hong; Ma, Hong; Xu, Jie; Tetrahedron Letters; vol. 50; nb. 15; (2009); p.

1677 - 1680 View in Reaxys With haem domains of cytochrome P450BM3 from Bacillus megaterium wild-type, NADPH, Enzymatic reaction Whitehouse, Christopher J. C.; Yang, Wen; Yorke, Jake A.; Rowlatt, Benjamin C.; Strong, Anthony J. F.; Blanford, Christopher F.; Bell, Stephen G.; Bartlam, Mark; Wong, Luet-Lok; Rao, Zihe; ChemBioChem; vol. 11; nb. 18; (2010); p.

2549 - 2556 View in Reaxys With Cr2O4 (2-)*Cu(2+), dihydrogen peroxide in acetonitrile, Time= 10h, T= 50 °C

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Acharyya, Shankha S.; Ghosh, Shilpi; Adak, Shubhadeep; Tripathi, Deependra; Bal, Rajaram; Catalysis Communications; vol. 59; (2015); p. 145 - 150 View in Reaxys With [Mn2(2,5-dihydroxyterephthalate)(H2O)2]·nH2O, oxygen in neat (no solvent), Time= 9h, T= 135 °C , Catalytic behavior, Time Kuwahara, Yasutaka; Yoshimura, Yukihiro; Yamashita, Hiromi; Dalton Transactions; vol. 46; nb. 26; (2017); p. 8415 8421 View in Reaxys

O

OH O

O

O

HO

Rx-ID: 42823231 View in Reaxys 4/141 Yield

Conditions & References

89 %Chromat.

General procedure for depyranylation General procedure: To a solution of THP-protected alcohols (1 mmol) in MeOH (1.0 mL), activated LUS-Pr-SO3H (0.02 g) was added, and the mixture was stirred at room temperature for an appropriate time as shown in Table 3. After the completion of the reaction,the mixture was dissolved in methanol and filtered to remove heterogeneous catalyst. The solvent was dried in vacuum, and the residue was subjected to column chromatography on silica to provide the pure product.

With LUS-Pr-SO3H, Time= 0.25h, T= 20 °C Rahimifard, Mahshid; Mohammadi Ziarani, Ghodsi; Badiei, Alireza; Research on Chemical Intermediates; vol. 42; nb. 7; (2016); p. 6327 - 6336 View in Reaxys

O

OH

OH

Rx-ID: 43213221 View in Reaxys 5/141 Yield 51 %

Conditions & References Stage 1: With dipotassium hydrogenphosphate, oxygen, Fukuzumi’s acridinium in chloroform, Time= 72h, T= 20 °C , Schlenk technique, Irradiation, Green chemistry Stage 2: With sodium tetrahydroborate in methanol, chloroform, Time= 0.5h, Green chemistry Song, Hai-Tao; Ding, Wei; Zhou, Quan-Quan; Liu, Jing; Lu, Liang-Qiu; Xiao, Wen-Jing; Journal of Organic Chemistry; vol. 81; nb. 16; (2016); p. 7250 - 7255 View in Reaxys

OH

O

Rx-ID: 43957326 View in Reaxys 6/141 Yield 85 %

Conditions & References Stage 1: With tert.-butyl lithium in tetrahydrofuran, pentane, Time= 0.333333h, T= -78 - -30 °C , Schlenk technique, Inert atmosphere, Wittig Rearrangement

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Stage 2: With water in tetrahydrofuran, pentane, T= -30 °C , Schlenk technique, Inert atmosphere, Wittig Rearrangement Velasco, Rocío; Silva López, Carlos; Nieto Faza, Olalla; Sanz, Roberto; Chemistry - A European Journal; vol. 22; nb. 42; (2016); p. 15058 - 15068 View in Reaxys

N

OH N HO Br

O

O

Br O

Rx-ID: 39244523 View in Reaxys 7/141 Yield

Conditions & References in acetonitrile, pH= 5.5, chemoselective reaction McGrath, Nicholas A.; Andersen, Kristen A.; Davis, Amy K. F.; Lomax, Jo E.; Raines, Ronald T.; Chemical Science; vol.

6; nb. 1; (2015); p. 752 - 755 View in Reaxys

N

OH Cl

O

Cl

OH

N

O

O

Cl

Cl

Rx-ID: 39244525 View in Reaxys 8/141 Yield

Conditions & References in acetonitrile, pH= 5.5, chemoselective reaction McGrath, Nicholas A.; Andersen, Kristen A.; Davis, Amy K. F.; Lomax, Jo E.; Raines, Ronald T.; Chemical Science; vol.

6; nb. 1; (2015); p. 752 - 755 View in Reaxys

N

OH N

O

O

O

HO

Rx-ID: 39244526 View in Reaxys 9/141 Yield

Conditions & References in acetonitrile, pH= 5.5, chemoselective reaction McGrath, Nicholas A.; Andersen, Kristen A.; Davis, Amy K. F.; Lomax, Jo E.; Raines, Ronald T.; Chemical Science; vol.

6; nb. 1; (2015); p. 752 - 755 View in Reaxys

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N

OH N

O

O

O

OH HO

OH

Rx-ID: 39244528 View in Reaxys 10/141 Yield

Conditions & References in acetonitrile, pH= 5.5, chemoselective reaction McGrath, Nicholas A.; Andersen, Kristen A.; Davis, Amy K. F.; Lomax, Jo E.; Raines, Ronald T.; Chemical Science; vol.

6; nb. 1; (2015); p. 752 - 755 View in Reaxys N

O

HO

N

O

N H O

OH

O O N H

O

O

Rx-ID: 39244530 View in Reaxys 11/141 Yield

Conditions & References in acetonitrile, pH= 5.5, chemoselective reaction McGrath, Nicholas A.; Andersen, Kristen A.; Davis, Amy K. F.; Lomax, Jo E.; Raines, Ronald T.; Chemical Science; vol.

6; nb. 1; (2015); p. 752 - 755 View in Reaxys

N

OH N

HO

SH

O

O

SH

O

Rx-ID: 39244532 View in Reaxys 12/141 Yield

Conditions & References in acetonitrile, pH= 5.5, chemoselective reaction McGrath, Nicholas A.; Andersen, Kristen A.; Davis, Amy K. F.; Lomax, Jo E.; Raines, Ronald T.; Chemical Science; vol.

6; nb. 1; (2015); p. 752 - 755 View in Reaxys

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N

OH

N

O O H O

N H

HO O

O

OH

O

NH

O

O

O OH

O

O

O

OH N H

O

O

Rx-ID: 39244548 View in Reaxys 13/141 Yield

Conditions & References in acetonitrile, pH= 5.5, chemoselective reaction McGrath, Nicholas A.; Andersen, Kristen A.; Davis, Amy K. F.; Lomax, Jo E.; Raines, Ronald T.; Chemical Science; vol.

6; nb. 1; (2015); p. 752 - 755 View in Reaxys

OH (v2)

H (v3)

OH

Rx-ID: 40515096 View in Reaxys 14/141 Yield

Conditions & References T= -270.16 °C , Kinetics Costa, Paolo; Trosien, Iris; Fernandez-Oliva, Miguel; Sanchez-Garcia, Elsa; Sander, Wolfram; Angewandte Chemie - International Edition; vol. 54; nb. 9; (2015); p. 2656 - 2660; Angew. Chem.; vol. 127; nb. 09; (2015); p. 2694 - 2698,5 View in Reaxys

OH B O

Rx-ID: 41524412 View in Reaxys 15/141 Yield 93 %

Conditions & References With sodium hydroxide in water, Inert atmosphere Eedugurala, Naresh; Wang, Zhuoran; Chaudhary, Umesh; Nelson, Nicholas; Kandel, Kapil; Kobayashi, Takeshi; Slowing, Igor I.; Pruski, Marek; Sadow, Aaron D.; ACS Catalysis; vol. 5; nb. 12; (2015); p. 7399 - 7414 View in Reaxys

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O O O

O

OH

O

O

Rx-ID: 34787223 View in Reaxys 16/141 Yield

Conditions & References 4. General procedure for copper-catalyzed benzylic oxidation (substrate scope) General procedure: A solution of copper(II) trifluoromethanesulfonate (11.1 mg, 0.03 mmol) and ligand 10a (8.4 mg, 0.036 mmol) in dry acetone (5 mL) was stirred at room temperature for 1 h. Phenylhydrazine (3.9 mg, 0.036 mmol) was added to this dark brown solution, and the solution became purple immediately. After stirring for additional 5 min, the benzylic substrate (3 mmol) and the oxidant tert-butyl benzoate (117 mg, 0.6 mmol) were then introduced successively. The mixture was stirred at 30 &deg;C for a certain time until the reaction was completed (determined by the disappearance of perester by TLC). After the solvent was evaporated in vacuum with a rotary evaporator, the residue was purified by silica gel chromatography using petrol ether/EtOAc as eluent to give the desired products.

With N-(quinolin-2-ylmethylidene)aniline, copper(II) bis(trifluoromethanesulfonate), phenylhydrazine in acetone, Time= 6h, T= 30 °C , Inert atmosphere, Schlenk technique Zhang, Bo; Zhu, Shou-Fei; Zhou, Qi-Lin; Tetrahedron; vol. 69; nb. 8; (2013); p. 2033 - 2037 View in Reaxys

OH

O B O

O

Rx-ID: 33150955 View in Reaxys 17/141 Yield

Conditions & References

300 mg

With hydrogenchloride, water in methanol, toluene, Time= 1h, Reflux, Inert atmosphere Arrowsmith, Merle; Hadlington, Terrance J.; Hill, Michael S.; Kociok-Koehn, Gabriele; Chemical Communications; vol.

48; nb. 38; (2012); p. 4567 - 4569 View in Reaxys O

OH

Rx-ID: 1834296 View in Reaxys 18/141 Yield 16 %, 84 %

Conditions & References With iodine, magnesium in methanol, Time= 2.5h, T= 20 °C , Title compound not separated from byproducts Khurana, Jitender M.; Bansal, Geeti; Kukreja, Gagan; Pandey, Ravi R.; Monatshefte fur Chemie; vol. 134; nb. 10; (2003); p. 1365 - 1371

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View in Reaxys 12 %, 84 %

With LiVH2 in tetrahydrofuran, Time= 12h, T= -78 - 20 °C Eisch, John J.; Fregene, Paul O.; Gitua, John N.; Journal of Organometallic Chemistry; vol. 692; nb. 21; (2007); p. 4647 4653 View in Reaxys

2 %, 81 %

With sodium tetrahydroborate, nickel dichloride in tetrahydrofuran, Time= 0.0833333h, T= 20 °C Khurana; Chauhan; Synthetic Communications; vol. 31; nb. 22; (2001); p. 3485 - 3489 View in Reaxys

38 %, 62 %

With samarium, 1,2-Diiodoethane in 1,2-dimethoxyethane, Time= 24h, Ambient temperature Oliver, H.; Chauvin, Y.; Saussine, L.; Tetrahedron; vol. 45; nb. 1; (1989); p. 165 - 170 View in Reaxys

47 %, 25 %

With C8K in 1,2-dimethoxyethane, Time= 1h, Ambient temperature Tamarkin, Dov; Rabinovitz, Mordecai; Journal of Organic Chemistry; vol. 52; nb. 15; (1987); p. 3472 - 3474 View in Reaxys

29 %Chromat., 16 %Chromat.

With [Ru(H2O)2(bipy)2](OTf)2, hydrogen in sulfolane, water, Time= 3h, T= 175 °C , p= 56887.8Torr Taher, Deeb; Thibault, Michelle E.; Di Mondo, Domenico; Jennings, Michael; Schlaf, Marcel; Chemistry - A European Journal; vol. 15; nb. 39; (2009); p. 10132 - 10143 View in Reaxys OH

O

O

OH

Rx-ID: 11013743 View in Reaxys 19/141 Yield 99 %

Conditions & References With [RuCl2(triphenylphosphine)((6-((3,5-dimethyl-pyrazol-1-yl)pyridin-2-yl)methylene)-p-tolyl-amine)]*0.5Et2O, potassium isopropoxide, Time= 5.16667h, T= 82 °C , p= 750.075Torr , Inert atmosphere Zhao, Miao; Yu, Zhengkun; Yan, Shenggang; Li, Yang; Journal of Organometallic Chemistry; vol. 694; nb. 19; (2009); p.

3068 - 3075 View in Reaxys

97 % Chromat.

With sodium hydroxide, RuCl2(PPh3)(iBu-BTP), Time= 9h, T= 82 °C , p= 750.075Torr Yu; Zeng; Sun; Deng; Dong; Chen; Wang; Pei; Journal of Organometallic Chemistry; vol. 692; nb. 11; (2007); p. 2306 - 2313 View in Reaxys

OH

OH

Rx-ID: 8997092 View in Reaxys 20/141 Yield 3.90 %, 22.6 %

Conditions & References With Escherichia coli JM109 harbouring pJ31BP-F275W in dimethyl sulfoxide, Time= 18h, T= 30 °C , L-medium, Enzymatic reaction Uchimura, Hiromasa; Horisaki, Tadafumi; Umeda, Takashi; Noguchi, Haruko; Usami, Yusuke; Li, Li; Terada, Tohru; Nakamura, Shugo; Shimizu, Kentaro; Takemura, Tetsuo; Habe, Hiroshi; Furihata, Kazuo; Omori, Toshio; Yamane, Hisakazu; Nojiri, Hideaki; Bioscience, Biotechnology and Biochemistry; vol. 72; nb. 12; (2008); p. 3237 - 3248

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View in Reaxys 3 mg, 10 mg

With E. coli (pHA171), isoropyl η-D-thiogalactopyranoside, ampicillin, D-glucose, vitamin B1 in various solvent(s), T= 30 °C Shindo; Ohnishi; Chun; Takahashi; Hayashi; Saito; Iguchi; Furukawa; Harayama; Horinouchi; Misawa; Bioscience, biotechnology, and biochemistry; vol. 65; nb. 11; (2001); p. 2472 - 2481 View in Reaxys O

OH

HO OH

Rx-ID: 28201388 View in Reaxys 21/141 Yield

Conditions & References

4 %, 5 %, With vanadium monochloride in tetrahydrofuran, Time= 12h, T= 25 °C , Inert atmosphere 32 %, 16 %, Eisch, John J.; Fregene, Paul O.; European Journal of Organic Chemistry; nb. 26; (2008); p. 4482 - 4492 43 % View in Reaxys 4 %Spectr., 5 %Spectr., 32 %Spectr., 16 %Spectr., 43 %Spectr.

With vanadium (I) chloride in tetrahydrofuran, Time= 12h, T= 20 °C Eisch, John J.; Fregene, Paul O.; Doetschman, David C.; European Journal of Organic Chemistry; nb. 16; (2008); p. 2825 2835 View in Reaxys

O

OH

HO OH

Rx-ID: 1834303 View in Reaxys 22/141 Yield 96 %, 2 %

Conditions & References With LiCrH4*2LiCl*2THF in tetrahydrofuran, Time= 12h, T= 25 °C Eisch, John J.; Shi, Xian; Alila, Joseph R.; Thiele, Sven; Chemische Berichte; vol. 130; nb. 9; (1997); p. 1175 - 1187 View in Reaxys

10 %, 63 %

With samarium, N-Bromosuccinimide in methanol, Time= 3h, T= 20 °C Banik, Bimal K.; Banik, Indrani; Samajdar, Susanta; Cuellar, Rogelio; Tetrahedron Letters; vol. 46; nb. 13; (2005); p. 2319 - 2322 View in Reaxys

60 %, 21 %

With tetrabutylammomium bromide, zinc(II) cation in N,N-dimethyl-formamide, Ambient temperature, electrolysis Fournier, Francoise; Fournier, Michel; Canadian Journal of Chemistry; vol. 64; (1986); p. 881 - 890

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View in Reaxys 37 %, 23 %

With samarium in methanol, Time= 8h, T= 20 °C , reductive coupling Ghatak, Anjan; Becker, Frederick F.; Banik, Bimal K.; Tetrahedron Letters; vol. 41; nb. 20; (2000); p. 3793 - 3796 View in Reaxys With [2,2]bipyridinyl, bis(1,5-cyclooctadiene)nickel (0) in tetrahydrofuran, 1.) 25 deg C, 30 min; 2.) reflux, 15 h

30 %, 25 %

Eisch, John J.; Qian, Yun; Singh, Mona; Journal of Organometallic Chemistry; vol. 512; nb. 1-2; (1996); p. 207 - 217 View in Reaxys 58 % Spectr., 42 % Spectr.

With ammonium hydroxide, titanium(III) chloride in methanol, Time= 0.0833333h, T= 20 - 25 °C , pH= 10 - 11 Clerici, Angelo; Pastori, Nadia; Porta, Ombretta; European Journal of Organic Chemistry; nb. 19; (2002); p. 3326 - 3335 View in Reaxys

O

O O F O 2

N

F

O

–O

S

N

F

N

O

N

O O

O

O

Ca 2+ O

OH

Rx-ID: 10101116 View in Reaxys 23/141 Yield 9 %, 1 %

Conditions & References in N,N-dimethyl-formamide, Time= 0.0833333h, UV-irradiation Player, Tomoko N.; Shinoda, Satoshi; Tsukube, Hiroshi; Organic and Biomolecular Chemistry; vol. 3; nb. 9; (2005); p. 1615 - 1616 View in Reaxys

OH

O

OH

HO

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22/58

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2-methyl-2'-formylbiphenyl2-hydroxymethyl-2'-formylbiphenyl

OH

Rx-ID: 10119266 View in Reaxys 24/141 Yield

Conditions & References T= 550 - 825 °C , p= 1Torr , flow-vacuum pyrolysis, Further byproducts given Istrati, Daniela; Marton, George; Draghici, Constantin; Grigore, Adriana; Banciu, Mircea D.; Revue Roumaine de Chimie; vol. 50; nb. 7-8; (2005); p. 719 - 724 View in Reaxys

O

O

O

N

O

N

Cl O

N

O

Na

N

O

O

O

OH

Rx-ID: 10152956 View in Reaxys 25/141 Yield 39 %, 2 %

Conditions & References in N,N-dimethyl-formamide, Time= 0.0833333h, UV-irradiation Player, Tomoko N.; Shinoda, Satoshi; Tsukube, Hiroshi; Organic and Biomolecular Chemistry; vol. 3; nb. 9; (2005); p. 1615 - 1616 View in Reaxys

OH

O O

Rx-ID: 9806339 View in Reaxys 26/141 Yield

Conditions & References With sodium hydroxide, urea in ethanol, Heating Mahmoodi, Nosrat O.; Khodaee, Ziba; Mendeleev Communications; vol. 14; nb. 6; (2004); p. 304 - 306

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View in Reaxys N N

O

NH 2

OH

N

N N

Rx-ID: 9292086 View in Reaxys 27/141 Yield

Conditions & References With tetraethylammonium hydroxide in dimethyl sulfoxide, T= 30 °C , Kinetics, Product distribution, Further Variations: Reagents, Solvents McDowell, Linda J.; Khodaei, M. Mehdi; Bethell, Donald; Organic and Biomolecular Chemistry; vol. 1; nb. 6; (2003); p. 995 - 1003 View in Reaxys Br O

N P

N

N

O

OH

N

Rx-ID: 9298314 View in Reaxys 28/141 Yield

Conditions & References T= 155 - 160 °C Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.; Organic and Biomolecular Chemistry; vol. 1; nb. 10; (2003); p. 1737 - 1740 View in Reaxys

O

Br

OH

Rx-ID: 9312470 View in Reaxys 29/141 Yield

Conditions & References With N,N,N,N,N,N-hexamethylphosphoric triamide, iron(II) oxalate dihydrate, Time= 0.166667h, T= 155 - 160 °C

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Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.; Organic and Biomolecular Chemistry; vol. 1; nb. 10; (2003); p. 1737 - 1740 View in Reaxys Br

N

O

O

OH

N

Rx-ID: 9333206 View in Reaxys 30/141 Yield

Conditions & References T= 155 - 160 °C Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.; Organic and Biomolecular Chemistry; vol. 1; nb. 10; (2003); p. 1737 - 1740 View in Reaxys N

O

OH

N

Rx-ID: 9503775 View in Reaxys 31/141 Yield

Conditions & References

45 %, 30 %

With tetrachloromethane, ammonia in water, dimethyl sulfoxide, T= 20 °C Korotchenko; Shastin; Nenaidenko; Balenkova; Russian Chemical Bulletin; vol. 52; nb. 2; (2003); p. 492 - 497 View in Reaxys NH 2 N

OH

Rx-ID: 13959275 View in Reaxys 32/141 Yield

Conditions & References Reaction Steps: 2 1: 30 percent / NH3; CCl4 / H2O; dimethylsulfoxide / 20 °C With tetrachloromethane, ammonia in water, dimethyl sulfoxide Korotchenko; Shastin; Nenaidenko; Balenkova; Russian Chemical Bulletin; vol. 52; nb. 2; (2003); p. 492 - 497 View in Reaxys Reaction Steps: 2 1: alcoholic sodium ethylate; air 2: concentrated hydrochloric acid; diluted alcohol With hydrogenchloride, air, ethanol, sodium ethanolate Staudinger; Gaule; Chemische Berichte; vol. 49; (1916); p. 1959 View in Reaxys

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O

OH

HO OH

Rx-ID: 9248489 View in Reaxys 33/141 Yield

Conditions & References With [(C5Me5)Ir(μ-H)]2 in toluene, Time= 18h, T= 65 °C Hou; Koizumi; Fujita; Yamazaki; Wakatsuki; Journal of the American Chemical Society; vol. 123; nb. 24; (2001); p. 5812 5813 View in Reaxys

O

O

OH

N

N 4

2

P

C N O– 2

Na +

Rx-ID: 11001275 View in Reaxys 34/141 Yield

Conditions & References

50 %, 50 %

Stage 1: With isopropyl alcohol in tetrahydrofuran, Time= 0.5h Stage 2: With hydrogenchloride in tetrahydrofuran, Further stages.

Hou, Zhaomin; Jia, Xueshun; Fujita, Akira; Tezuka, Hiroaki; Yamazaki, Hiroshi; Wakatsuki, Yasuo; Chemistry - A European Journal; vol. 6; nb. 16; (2000); p. 2994 - 3005 View in Reaxys O

OH

Rx-ID: 5191270 View in Reaxys 35/141 Yield 1 %, 2 %, 7 %, 71 %

Conditions & References With pyridine, titanium tetrachloride, zinc in tetrahydrofuran, Time= 21h, Heating, Reduction, trimerization, Further byproducts given Pogodin, Sergey; Cohen, Shmuel; Agranat, Israel; European Journal of Organic Chemistry; nb. 8; (1999); p. 1979 - 1984 View in Reaxys

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O–

OH O

C–

2

2

Na +

Rx-ID: 4913267 View in Reaxys 36/141 Yield

Conditions & References

98 %

With water Hou, Zhaomin; Fujita, Akira; Yamazaki, Hiroshi; Wakatsuki, Yasuo; Chemical Communications; nb. 6; (1998); p. 669 670 View in Reaxys

OH

O

O O

Rx-ID: 4984583 View in Reaxys 37/141 Yield

Conditions & References With tert.-butylhydroperoxide, tetrabutylammomium bromide, copper dichloride in dichloromethane, water, Time= 4h, T= 25 °C , Yield given. Yields of byproduct given Rothenberg, Gadi; Feldberg, Liron; Wiener, Harold; Sasson, Yoel; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (1998); p. 2429 - 2434 View in Reaxys

O

O

OH O

Si

Rx-ID: 1834157 View in Reaxys 38/141 Yield

Conditions & References With ytterbium, methyl iodide, 1.) THF, r.t., 2 h, 2.) THF, 40 deg C, 2 h, Yield given. Multistep reaction. Yields of byproduct given Taniguchi, Yuki; Nagafuji, Akihiro; Makioka, Yoshikazu; Takaki, Ken; Fujiwara, Yuzo; Tetrahedron Letters; vol. 35; nb.

37; (1994); p. 6897 - 6898 View in Reaxys

O

OH O

Rx-ID: 1834301 View in Reaxys 39/141

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Yield

Conditions & References With benzoyltrimethylsilane, ytterbium, methyl iodide, 1.) THF, r.t., 2 h, 2.) THF, 40 deg C, 2 h, Yield given. Multistep reaction.

Yields of byproduct given Taniguchi, Yuki; Nagafuji, Akihiro; Makioka, Yoshikazu; Takaki, Ken; Fujiwara, Yuzo; Tetrahedron Letters; vol. 35; nb.

37; (1994); p. 6897 - 6898 View in Reaxys O O

O

OH O

O

P

O

Rx-ID: 1834302 View in Reaxys 40/141 Yield

Conditions & References

0.25 g, 0.8 g, 0.85 g

With acetic acid, phosphorous acid trimethyl ester, Time= 24h, Ambient temperature, var. temp. and time, Mechanism Fuzhenkova, A. V.; Tyryshkin, N. I.; Russian Journal of General Chemistry; vol. 63; nb. 1.1; (1993); p. 76 - 80; Zhurnal Obshchei Khimii; vol. 63; nb. 1; (1993); p. 106 - 110 View in Reaxys

0.25 g, 0.8 g, 0.85 g

With acetic acid, phosphorous acid trimethyl ester, Time= 24h, Ambient temperature Fuzhenkova, A. V.; Tyryshkin, N. I.; Russian Journal of General Chemistry; vol. 63; nb. 1.1; (1993); p. 76 - 80; Zhurnal Obshchei Khimii; vol. 63; nb. 1; (1993); p. 106 - 110 View in Reaxys

O

Ge Li

OH

Ge

GeH

Ge

Ge Cl

Rx-ID: 26491847 View in Reaxys 41/141 Yield

Conditions & References

24 %, 33 %, With hydrogenchloride in tetrahydrofuran, inert atmosphere; addn. of org. compd. soln. to soln. of Ge-compd. at 0°C, mixt.

68 %, <1 keeping at 0°C for 30 min, at room temp. for 2 h, warming (40°C, 1.5 h), soln. hydrolysis (HCl); soln. extn. (ether), drying (Na2SO4), soln. concn. (reduced pressure), redissoln. (THF); (1)H-NMR Riviere, P.; Castel, A.; Desor, D.; Abdennadher, C.; Journal of Organometallic Chemistry; vol. 443; nb. 1; (1993); p. 51 - 60 ; (from Gmelin) View in Reaxys

O

Ge Li

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OH

Ge

Ge

Ge Cl

Rx-ID: 26491848 View in Reaxys 42/141 Yield

Conditions & References

20 %, <1, 60 %

With hydrogenchloride in diethyl ether, inert atmosphere; addn. of Ge-compd. soln. to soln. of org. compd. at -10°C, keeping for 30 min, soln. allowing to stay at room temp. for 40 min, soln. hydrolysis (HCl); soln. extn. (ether), drying (Na2SO4), soln. concn. (reduced pressure); (1)H-NMR Riviere, P.; Castel, A.; Desor, D.; Abdennadher, C.; Journal of Organometallic Chemistry; vol. 443; nb. 1; (1993); p. 51 - 60 ; (from Gmelin) View in Reaxys OH H C+

Rx-ID: 2293090 View in Reaxys 43/141 Yield

Conditions & References With perchloric acid, sodium perchlorate, water in various solvent(s), T= 25 °C , Rate constant, Equilibrium constant Amyes, Tina L.; Richard, John P.; Novak, Michael; Journal of the American Chemical Society; vol. 114; nb. 21; (1992); p.

8032 - 8041 View in Reaxys OH

Br

Rx-ID: 308617 View in Reaxys 44/141 Yield

Conditions & References

40 %

With acetonitrile, Time= 0.166667h, Irradiation, Mechanism, Quantum yield Wan, Peter; Krogh, Erik; Journal of the American Chemical Society; vol. 111; nb. 13; (1989); p. 4887 - 4895 View in Reaxys With potassium carbonate Loevenich; Becker; Schroeder; Journal fuer Praktische Chemie (Leipzig); vol. <2> 127; (1930); p. 248,257 View in Reaxys With water, lead(II) oxide Loevenich; Becker; Schroeder; Journal fuer Praktische Chemie (Leipzig); vol. <2> 127; (1930); p. 248,257 View in Reaxys O

OH

HO OH

Rx-ID: 1834294 View in Reaxys 45/141

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Yield

Conditions & References

18 %, 5 %, 76 %

With samarium, 1,2-Diiodoethane in 1,2-dimethoxyethane, Time= 4h, Ambient temperature, reversibility, further rare earth metals, different molar ratios, Product distribution Oliver, H.; Chauvin, Y.; Saussine, L.; Tetrahedron; vol. 45; nb. 1; (1989); p. 165 - 170 View in Reaxys

18 %, 5 %, 76 %

With samarium, 1,2-Diiodoethane in 1,2-dimethoxyethane, Time= 4h, Ambient temperature Oliver, H.; Chauvin, Y.; Saussine, L.; Tetrahedron; vol. 45; nb. 1; (1989); p. 165 - 170 View in Reaxys O

OH

HO OH

Rx-ID: 1834295 View in Reaxys 46/141 Yield

Conditions & References

84 %, 13 %

With samarium, 1,2-Diiodoethane in 1,2-dimethoxyethane, Time= 24h, Ambient temperature Oliver, H.; Chauvin, Y.; Saussine, L.; Tetrahedron; vol. 45; nb. 1; (1989); p. 165 - 170 View in Reaxys

O OH O

Rx-ID: 2046676 View in Reaxys 47/141 Yield

Conditions & References

80 %, 20 %

With acetonitrile, Time= 0.166667h, Irradiation, Mechanism, Product distribution, Quantum yield Wan, Peter; Krogh, Erik; Journal of the American Chemical Society; vol. 111; nb. 13; (1989); p. 4887 - 4895 View in Reaxys O

O

OH

OH HO

OH

HO

Rx-ID: 1460897 View in Reaxys 48/141 Yield

Conditions & References With ytterbium, 1.) THF, HMPA, RT, 2.) RT, 2 h, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys

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30/58

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O O

OH OH

HO

HO

HO

Rx-ID: 1461030 View in Reaxys 49/141 Yield

Conditions & References With ytterbium, 1.) THF, HMPA, RT, 2.) RT, 2 h, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys

O

OH OH HO

O

Rx-ID: 1569171 View in Reaxys 50/141 Yield 16 %, 61 %

Conditions & References With ytterbium in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 2.33333h, Ambient temperature Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 668 - 670 View in Reaxys With ytterbium, 1.) THF, HMPA, RT, 2.) RT, 2 h, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys O

O

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O

OH

HO

OH

OH

Rx-ID: 1753300 View in Reaxys 51/141 Yield

Conditions & References With n-butyllithium, 1.) THF, hexane, -65 deg C; 2.) RT, 6 d, Yield given. Multistep reaction. Yields of byproduct given Sommer, Andreas; Stamm, Helmut; Woderer, Anton; Chemische Berichte; vol. 121; (1988); p. 387 - 390 View in Reaxys O

OH

HO

OH

OH

Rx-ID: 1768983 View in Reaxys 52/141 Yield

Conditions & References With n-butyllithium, 1.) THF, hexane, -65 deg C; 2.) RT, 10 min, Yield given. Multistep reaction. Yields of byproduct given Sommer, Andreas; Stamm, Helmut; Woderer, Anton; Chemische Berichte; vol. 121; (1988); p. 387 - 390 View in Reaxys O

O

O

O

O

OH HO

OH

OH

Rx-ID: 1834150 View in Reaxys 53/141 Yield 61 %, 5 %, 15 %

Conditions & References With ytterbium in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 0.833333h, p= 760Torr , Ambient temperature Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 668 - 670 View in Reaxys With ytterbium, 1.) THF, HMPA, RT, 2.) RT, 1 atm, 30 min, Yield given. Multistep reaction. Yields of byproduct given

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Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys

O

OH

HO

OH

OH

Rx-ID: 1834304 View in Reaxys 54/141 Yield

Conditions & References

20 %, 9 %, 63 %

With n-butyllithium in tetrahydrofuran, hexane, multistep reaction: 1.) -65 deg C;2.) RT, 10 min; other time, other products, Product distribution Sommer, Andreas; Stamm, Helmut; Woderer, Anton; Chemische Berichte; vol. 121; (1988); p. 387 - 390 View in Reaxys

HO

OH

O

HO

O

Rx-ID: 2328387 View in Reaxys 55/141 Yield

Conditions & References

24 %, 58 %

With ytterbium in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 2.33333h, Ambient temperature Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 668 - 670 View in Reaxys With ytterbium, 1.) THF, HMPA, RT, 2.) RT, 2 h, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys

O

O

OH HO HO

Rx-ID: 2340371 View in Reaxys 56/141 Yield

Conditions & References With ytterbium, 1.) THF, HMPA, RT, 2.) RT, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys

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OH

O

O HO

N

Rx-ID: 2409249 View in Reaxys 57/141 Yield

Conditions & References With ytterbium, 1.) THF, HMPA, RT, 2.) RT, 4 h, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys

O

OH

HO

N

O

Rx-ID: 2937074 View in Reaxys 58/141 Yield

Conditions & References With ytterbium, 1.) THF, HMPA, RT, 2.) RT, 4 h, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys

O

OH HO

O

OH

Rx-ID: 3523228 View in Reaxys 59/141 Yield

Conditions & References With ytterbium, 1.) THF, HMPA, RT, 2.) RT, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys O O

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OH

OH HO

Rx-ID: 3541075 View in Reaxys 60/141 Yield

Conditions & References

8 %, 88 %

With ytterbium in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 0.833333h, Ambient temperature Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 668 - 670 View in Reaxys With ytterbium, 1.) THF, HMPA, RT, 2.) RT, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys

O

OH HO

O

N

Rx-ID: 3737544 View in Reaxys 61/141 Yield

Conditions & References

46 %, 53 %

With ytterbium in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 4.33333h, Ambient temperature Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 668 - 670 View in Reaxys With ytterbium, 1.) THF, HMPA, RT, 2.) RT, 4 h, Yield given. Multistep reaction. Yields of byproduct given Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of Organic Chemistry; vol. 53; nb. 26; (1988); p. 6077 - 6084 View in Reaxys N N

O

OH

N N

Rx-ID: 3935862 View in Reaxys 62/141 Yield

Conditions & References With 4-methyl-phenol-formaldehyde resin in cyclohexanone, Irradiation, also thermolysis

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Thurner, Joern-Uwe; Donau, Ralf; Wolff, Monika; Tomaschewski, Georg; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 28; nb. 10; (1988); p. 373 - 374 View in Reaxys

OH

O

HO

O

Rx-ID: 3953645 View in Reaxys 63/141 Yield

Conditions & References

46 %, 53 %

With ytterbium in tetrahydrofuran, N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 4.33333h, Ambient temperature Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 668 - 670 View in Reaxys

O O O O

O

OH

O O

Rx-ID: 2077256 View in Reaxys 64/141 Yield

Conditions & References

16 %, 5 %, 30 %, 30 %

With C8K in tetrahydrofuran, T= 25 °C Tamarkin, Dov; Rabinovitz, Mordecai; Journal of Organic Chemistry; vol. 52; nb. 15; (1987); p. 3472 - 3474 View in Reaxys

27 %, 4 %, 19 %, 13 %

With C8K in 1,2-dimethoxyethane, T= 25 °C Tamarkin, Dov; Rabinovitz, Mordecai; Journal of Organic Chemistry; vol. 52; nb. 15; (1987); p. 3472 - 3474 View in Reaxys

Si

OH

O

Rx-ID: 1995626 View in Reaxys 65/141 Yield

Conditions & References With hydrogenchloride in methanol, Ambient temperature, Yield given Taddei, Maurizio; Ricci, Alfredo; Synthesis; nb. 8; (1986); p. 633 - 635 View in Reaxys

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OH O O

Rx-ID: 2845259 View in Reaxys 66/141 Yield

Conditions & References With lithium aluminium tetrahydride Muzart, Jacques; Tetrahedron Letters; vol. 27; nb. 27; (1986); p. 3139 - 3142 View in Reaxys

O

OH

N

(v4) (v5)

H Si O Si H (v5) (v4)

N

Rx-ID: 3953646 View in Reaxys 67/141 Yield

Conditions & References

100 %

With 8-(N,N-dimethylaminomethyl)-1-naphthyl-(Ph)SiH2, Time= 12h, T= 25 °C Boyer, J.; Breliere, C.; Corriu, R. J. P.; Kpoton, A.; Poirier, M.; Royo, G.; Journal of Organometallic Chemistry; vol. 311; (1986); p. C39 - C43 View in Reaxys

O

O HO

OH

OH

HO OH

Rx-ID: 1748224 View in Reaxys 68/141 Yield 4 %, 95 %, 1%

Conditions & References With copper(I) oxide in acetonitrile, T= 50 °C Toussaint, Olivier; Capdevielle, Patrice; Maumy, Michel; Tetrahedron; vol. 40; nb. 17; (1984); p. 3229 - 3234 View in Reaxys OH

(v2)

Yb

I

Rx-ID: 1767504 View in Reaxys 69/141 Yield

Conditions & References With oxygen, multistep reaction for investigating reactivity of CH3IYb; further reactant, Product distribution Yokoo, Kazuhiri; Kijima, Yasushi; Fujiwara, Yuzo; Taniguchi, Hiroshi; Chemistry Letters; (1984); p. 1321 - 1322

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View in Reaxys

O

OH Al HO

Rx-ID: 1834235 View in Reaxys 70/141 Yield

Conditions & References

53 %, 76 %

in n-heptane, Time= 8h, Heating Eisch, John J.; Fichter, Kenneth C.; Journal of Organic Chemistry; vol. 49; nb. 24; (1984); p. 4631 - 4639 View in Reaxys

O

OH

OH

HO OH

Rx-ID: 1834305 View in Reaxys 71/141 Yield

Conditions & References

48 %, 38 %

With chromium chloride, tetrabutylammomium bromide in N,N-dimethyl-formamide, T= 20 °C , electrolysis Fournier, F.; Berthelot, J.; Pascal, Y. L.; Tetrahedron; vol. 40; nb. 2; (1984); p. 339 - 347 View in Reaxys OH

(v2)

Yb

I

Rx-ID: 3364821 View in Reaxys 72/141 Yield

Conditions & References With oxygen, 1.) THF, -20 deg C; 2.) THF, -20 deg C, Yield given. Multistep reaction Yokoo, Kazuhiri; Kijima, Yasushi; Fujiwara, Yuzo; Taniguchi, Hiroshi; Chemistry Letters; (1984); p. 1321 - 1322 View in Reaxys N N

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OH

O

N N

Rx-ID: 3935868 View in Reaxys 73/141 Yield

Conditions & References

1.3 % Chromat., 87.4 % Chromat., 10.9 % Chromat.

With tetramethylammonium tetrafluoroborate in acetonitrile, T= 30 °C , electrochemical reaction, Further byproducts given. Title compound not separated from byproducts

1.2 % Chromat., 34.6 % Chromat., 63.8 % Chromat.

With tris(p-bromophenylammoniumyl) hexachloroantimonate in acetonitrile, T= 30 °C , Further byproducts given. Title compound not separated from byproducts

Ahmad, Iftikhar; Bethell, Donald; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1527 - 1530 View in Reaxys

Ahmad, Iftikhar; Bethell, Donald; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1527 - 1530 View in Reaxys N

O N

OH

N N

HO OH

Rx-ID: 3935869 View in Reaxys 74/141 Yield

Conditions & References

2.1 % Chromat., 62.8 % Chromat., 33.5 % Chromat.

With copper(II) bis(tetrafluoroborate) in acetonitrile, T= 30 °C , decomposition under electrochemical conditions or by various chemical oxidants with their various concentration, Product distribution, Rate constant

1.2 % Chromat., 34.6 % Chromat., 63.8 % Chromat.

With tris(p-bromophenylammoniumyl) hexachloroantimonate in acetonitrile, T= 30 °C , variation of catalyst concentration, Product distribution, Rate constant

Ahmad, Iftikhar; Bethell, Donald; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1527 - 1530 View in Reaxys

Ahmad, Iftikhar; Bethell, Donald; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1527 - 1530 View in Reaxys

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N

OH

O N

N N

Rx-ID: 3935870 View in Reaxys 75/141 Yield

Conditions & References

0.29 % Chromat., 0.25 % Chromat., 92.5 % Chromat.

With tetramethylammonium tetrafluoroborate in acetonitrile, Time= 0.0666667h, T= 30 °C , decomposition under the conditions of interrupted constant-current electrolysis (i.c.c.e.), the effect of air, oxygen and other additives (diethyl malonate, tetralin), Product distribution, Rate constant, Mechanism Bethell, Donald; McDowall, Linda J.; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1531 - 1536 View in Reaxys With tetramethylammonium tetrafluoroborate in [D3]acetonitrile, Time= 0.0666667h, T= 30 °C , decomposition under the conditions of interrupted constant-current electrolysis (i.c.c.e.), Rate constant Bethell, Donald; McDowall, Linda J.; Parker, Vernon D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1984); p. 1531 - 1536 View in Reaxys

O

O

OH

HO OH

O

Rx-ID: 1834318 View in Reaxys 76/141 Yield

Conditions & References

48 %, 38 %

With chromium (III) ion, tetrabutylammomium bromide in N,N-dimethyl-formamide, T= 20 °C Fournier, Francoise; Berthelot, Jacques; Pascal, Yves-Louis; Canadian Journal of Chemistry; vol. 61; (1983); p. 2121 - 2125 View in Reaxys O Cl Cl O

Cl

N

O

OH

O

O

HO

O

O

O

Rx-ID: 3790310 View in Reaxys 77/141

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Yield

Conditions & References

11 %, 5 %, 8 %, 17 %

electrochemical reduction, Further byproducts given Degrand, Chantal; Belot, Gerard; Compagnon, Paul-Louis; Gasquez, Francoise; Canadian Journal of Chemistry; vol. 61; (1983); p. 2581 - 2589 View in Reaxys

O

OH Si HO Si Br

Rx-ID: 1834139 View in Reaxys 78/141 Yield

Conditions & References With magnesium, 1) ether, 2) ether, 2 h, reflux, Yield given. Multistep reaction Birkofer, Leonard; Kittler, Juergen; Chemische Berichte; vol. 115; nb. 12; (1982); p. 3737 - 3746 View in Reaxys O Cl Cl O

Cl

Cl

O

OH

O

O O

O O

O

O

Rx-ID: 3790311 View in Reaxys 79/141 Yield 11 %, 3.5 %, 8 %, 17 %

Conditions & References in acetonitrile, electrochemical reduction: mercury cathode, -1.35 V, Further byproducts given Belot, Gerard; Degrand, Chantal; Compagnon, Paul-Louis; Journal of Organic Chemistry; vol. 47; nb. 2; (1982); p. 325 331 View in Reaxys OH

Rx-ID: 7025291 View in Reaxys 80/141 Yield

Conditions & References Lombardo,L. et al.; Australian Journal of Chemistry; vol. 31; (1978); p. 1585 - 1605 View in Reaxys Mathieu,A.; Bulletin de la Societe Chimique de France; (1971); p. 1526 - 1533 View in Reaxys Bolton,R. et al.; Journal of the Chemical Society; (1964); p. 1895 - 1906 View in Reaxys Friedrich,E.C.; Taggart,D.B.; Journal of Organic Chemistry; vol. 43; nb. 5; (1978); p. 805 - 808

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View in Reaxys Eisch,J.J. et al.; Journal of Organometallic Chemistry; vol. 65; (1974); p. 289 - 301 View in Reaxys Russel et al.; Journal of the American Chemical Society; vol. 86; (1964); p. 1807,1812 View in Reaxys Russel et al.; Journal of the American Chemical Society; vol. 84; (1962); p. 4155,4156 View in Reaxys Adamski; Cannon; Journal of Organic Chemistry; vol. 29; (1964); p. 3693,3694 View in Reaxys Bunyan; Hey; Journal of the Chemical Society; (1962); p. 2771,2774 View in Reaxys Lansbury; Peterson; Journal of the American Chemical Society; vol. 85; (1963); p. 2236,2242 View in Reaxys Sayigh; Journal of Organic Chemistry; vol. 25; (1960); p. 1707 View in Reaxys Bunyan et al.; Journal of the Chemical Society; (1962); p. 324,330 View in Reaxys Schenker; Angewandte Chemie; vol. 73; (1961); p. 81,105 View in Reaxys Nakagawa; Minami; Tetrahedron Letters; (1972); p. 343,345 View in Reaxys Thakar; Rao; Journal of Scientific and Industrial Research, Section B: Physical Sciences; vol. 21; (1962); p. 583,586 View in Reaxys Caubere; Moreau; Bulletin de la Societe Chimique de France; (1971); p. 3276,3278, 3281 View in Reaxys Scretlas; Cazianis; Tetrahedron; vol. 34; (1978); p. 933,935,939 View in Reaxys Parsons; Cohen; Journal of the American Chemical Society; vol. 96; (1974); p. 2948,2950,2951 View in Reaxys Davies; Hodge; Journal of the Chemical Society [Section] C: Organic; (1971); p. 3158,3163,3164 View in Reaxys Inoue et al.; Journal of the Chemical Society, Chemical Communications; (1977); p. 412 View in Reaxys Cerny; Malek; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 842,844,845,850,851 View in Reaxys Kajigaeshi; Nippon Kagaku Zasshi; vol. 83; (1962); p. 191,193; ; vol. 59; nb. 523d View in Reaxys Thompson; Chemistry and Industry (London, United Kingdom); (1968); p. 184 View in Reaxys Warren; Journal of the Chemical Society; (1961); p. 2561,2563 View in Reaxys Kajigaeshi; Nippon Kagaku Zasshi; vol. 82; (1961); p. 1397,1399; ; vol. 59; nb. 2736; (1963) View in Reaxys Davidson et al.; Journal of the Chemical Society [Section] C: Organic; (1971); p. 3480 View in Reaxys Pietra; Tacconi; Farmaco, Edizione Scientifica; vol. 15; (1960); p. 451,466 View in Reaxys Campbell; Wolfe; Organic Preparations and Procedures International; vol. 3; (1971); p. 303 View in Reaxys O

OH Al3+

O–

3

Rx-ID: 164724 View in Reaxys 81/141 Yield

Conditions & References T= 150 °C Macbeth; Mills; Journal of the Chemical Society; (1949); p. 2646,2648

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View in Reaxys O

OH Al3+

–O

3

Rx-ID: 164726 View in Reaxys 82/141 Yield

Conditions & References T= 105 - 110 °C Macbeth; Mills; Journal of the Chemical Society; (1949); p. 2646,2648 View in Reaxys OH

O

LiAlH4

O

Rx-ID: 7025296 View in Reaxys 83/141 Yield

Conditions & References T= 35 °C Hochstein; Journal of the American Chemical Society; vol. 71; (1949); p. 305 View in Reaxys

OH

Br –O

O Na +

O

Rx-ID: 308612 View in Reaxys 84/141 Yield

Conditions & References With acetic acid Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371 View in Reaxys

OH

Br

O

Rx-ID: 308618 View in Reaxys 85/141 Yield

Conditions & References With sodium acetate, acetic acid Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371

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View in Reaxys Br –O

O

O

OH

Na +

OH

O

Rx-ID: 639941 View in Reaxys 86/141 Yield

Conditions & References Wittig; Vidal; Chemische Berichte; vol. 81; (1948); p. 368,371 View in Reaxys O

OH

OH

nickel /kieselguhr

Rx-ID: 7025298 View in Reaxys 87/141 Yield

Conditions & References T= 70 - 75 °C , p= 84583.4Torr , Hydrogenation Hurd; Mold; Journal of Organic Chemistry; vol. 13; (1948); p. 339,342 View in Reaxys O

aq.-ethanolic KOH

palladium/charcoal

OH

Rx-ID: 7025300 View in Reaxys 88/141 Yield

Conditions & References Hydrogenation Forrest; Tucker; Journal of the Chemical Society; (1948); p. 1137,1140 View in Reaxys O

OH

aq.-ethanolic KOH

Raney nickel

Rx-ID: 7025302 View in Reaxys 89/141

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Yield

Conditions & References Hydrogenation Forrest; Tucker; Journal of the Chemical Society; (1948); p. 1137,1140 View in Reaxys O

OH Al3+

–O

HO

3

Rx-ID: 791281 View in Reaxys 90/141 Yield

Conditions & References Ferrier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 220; (1945); p. 460 View in Reaxys OH

O Al3+

OH

O–

3

Rx-ID: 741742 View in Reaxys 91/141 Yield

Conditions & References Lund; Chemische Berichte; vol. 70; (1937); p. 1520,1524 View in Reaxys Baker; Adkins; Journal of the American Chemical Society; vol. 62; (1940); p. 3305,3306 View in Reaxys OH

O

HO OH

KO H

Rx-ID: 7025295 View in Reaxys 92/141 Yield

Conditions & References T= 170 - 180 °C Huntress; Seikel; Journal of the American Chemical Society; vol. 61; (1939); p. 816,819 View in Reaxys O

OH

methanol. KOH

Rx-ID: 7025297 View in Reaxys 93/141 Yield

Conditions & References Huntress; Seikel; Journal of the American Chemical Society; vol. 61; (1939); p. 816,819 View in Reaxys

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OH O

OH O

ethanolic KOH

Rx-ID: 7044884 View in Reaxys 94/141 Yield

Conditions & References Huntress; Seikel; Journal of the American Chemical Society; vol. 61; (1939); p. 816,819 View in Reaxys OH O

OH O HO OH

KO H

Rx-ID: 7044885 View in Reaxys 95/141 Yield

Conditions & References T= 180 °C Huntress; Seikel; Journal of the American Chemical Society; vol. 61; (1939); p. 816,819 View in Reaxys O–

O

C

Na +

O

OH

HO OH

Rx-ID: 628888 View in Reaxys 96/141 Yield

Conditions & References Mechanismus.Hydrolysis Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 1185,2827, 2829 View in Reaxys Bent; Irwin; Journal of the American Chemical Society; vol. 58; (1936); p. 2072 View in Reaxys

OH

Se+

H

H O

Br–

Se

Rx-ID: 7980426 View in Reaxys 97/141

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References Hughes; Kuriyan; Journal of the Chemical Society; (1935); p. 1609,1611 View in Reaxys

OH

HO OH

Rx-ID: 314678 View in Reaxys 98/141 Yield

Conditions & References With sodium amalgam, diethyl ether, benzene Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 355,358 View in Reaxys With alcoholic alkali Kliegl; Chemische Berichte; vol. 62; (1929); p. 1330; Chemische Berichte; vol. 64; (1931); p. 2422 View in Reaxys O

OH O–

OH

Na +

Rx-ID: 741741 View in Reaxys 99/141 Yield

Conditions & References Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 391,394 View in Reaxys

O–

HO

Na +

OH

O

O

OH

Rx-ID: 847019 View in Reaxys 100/141 Yield

Conditions & References unter Luftausschluss Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 355,358 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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HO

sodium-amalgam

OH

O

OH

Rx-ID: 7156383 View in Reaxys 101/141 Yield

Conditions & References Bachmann; Journal of the American Chemical Society; vol. 55; (1933); p. 355,358 View in Reaxys O

OH

Br Mg

Rx-ID: 59159 View in Reaxys 102/141 Yield

Conditions & References With benzene Schlenk; Chemische Berichte; vol. 64; (1931); p. 739,743 View in Reaxys O

OH HO

Br Mg

Rx-ID: 59160 View in Reaxys 103/141 Yield

Conditions & References Schlenk; Chemische Berichte; vol. 64; (1931); p. 739,743 View in Reaxys With benzene Schlenk; Chemische Berichte; vol. 64; (1931); p. 739,743 View in Reaxys O

OH Cl Mg

Rx-ID: 164716 View in Reaxys 104/141 Yield

Conditions & References With benzene Schlenk; Chemische Berichte; vol. 64; (1931); p. 739,743 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O

OH HO

Cl Mg

Rx-ID: 164717 View in Reaxys 105/141 Yield

Conditions & References Schlenk; Chemische Berichte; vol. 64; (1931); p. 739,743 View in Reaxys With benzene Schlenk; Chemische Berichte; vol. 64; (1931); p. 739,743 View in Reaxys OH

O

octyl magnesium iodide

Rx-ID: 7025299 View in Reaxys 106/141 Yield

Conditions & References With benzene Schlenk; Chemische Berichte; vol. 64; (1931); p. 739,743 View in Reaxys Br

H

H

aqueous K2CO3-solution

O

OH

Rx-ID: 7156384 View in Reaxys 107/141 Yield

Conditions & References Loevenich; Becker; Schroeder; Journal fuer Praktische Chemie (Leipzig); vol. <2> 127; (1930); p. 248,257 View in Reaxys OH

Br

H

H O

PbO

Rx-ID: 7156385 View in Reaxys 108/141 Yield

Conditions & References Loevenich; Becker; Schroeder; Journal fuer Praktische Chemie (Leipzig); vol. <2> 127; (1930); p. 248,257 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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OH

S+

H

H

Br–

O

S

Rx-ID: 7980425 View in Reaxys 109/141 Yield

Conditions & References Ingold; Jessop; Journal of the Chemical Society; (1930); p. 708,711 View in Reaxys O

OH O

OH

zinc dust

Rx-ID: 7025305 View in Reaxys 110/141 Yield

Conditions & References Kliegl; Chemische Berichte; vol. 62; (1929); p. 1330; Chemische Berichte; vol. 64; (1931); p. 2422 View in Reaxys

O

HO

OH

alcoholic alkali

OH

Rx-ID: 7156386 View in Reaxys 111/141 Yield

Conditions & References Kliegl; Chemische Berichte; vol. 62; (1929); p. 1330; Chemische Berichte; vol. 64; (1931); p. 2422 View in Reaxys OH

fluorenone disodium

Rx-ID: 7025294 View in Reaxys 112/141 Yield

Conditions & References With diethyl ether, ethanol, Hydrolysis Schlenk; Bergmann; Justus Liebigs Annalen der Chemie; vol. 463; (1928); p. 208 View in Reaxys O OH O

O

O

OH

Rx-ID: 189985 View in Reaxys 113/141 Yield

Conditions & References T= 200 °C

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Kliegl; Wuensch; Weigele; Chemische Berichte; vol. 59; (1926); p. 640 View in Reaxys

O O

OH O

O

OH O

O

O

HO

OH H 2N 2 O

Rx-ID: 193321 View in Reaxys 114/141 Yield

Conditions & References T= 200 °C , im Rohr Kliegl; Wuensch; Weigele; Chemische Berichte; vol. 59; (1926); p. 640 View in Reaxys O OH O

Rx-ID: 294828 View in Reaxys 115/141 Yield

Conditions & References With ethanol, T= 200 °C Kliegl; Wuensch; Weigele; Chemische Berichte; vol. 59; (1926); p. 640 View in Reaxys

OH O

O O

O OH

alcoholic KOH-solution

O

Rx-ID: 7980424 View in Reaxys 116/141 Yield

Conditions & References Kliegl; Wuensch; Weigele; Chemische Berichte; vol. 59; (1926); p. 640 View in Reaxys

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only.

Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O O

alcoholic KOH-solution

O

O

O

OH HO

OH

O

OH

Rx-ID: 8255006 View in Reaxys 117/141 Yield

Conditions & References Kliegl; Wuensch; Weigele; Chemische Berichte; vol. 59; (1926); p. 640 View in Reaxys OH N O

OH

zinc dust

O

OH

NH 2 HN

Rx-ID: 7049199 View in Reaxys 118/141 Yield

Conditions & References Kuhn; Jacob; Chemische Berichte; vol. 58; (1925); p. 1437 View in Reaxys O OH O

Cl

HO

Cl

OH

H

H 2N 2 O

Rx-ID: 7185012 View in Reaxys 119/141 Yield

Conditions & References Kuhn; Wassermann; Chemische Berichte; vol. 58; (1925); p. 2230 View in Reaxys O

amalgamated aluminium

O

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OH

Rx-ID: 7025293 View in Reaxys 120/141 Yield

Conditions & References Sieglitz; Jassoy; Chemische Berichte; vol. 55; (1922); p. 2039 View in Reaxys O

OH

OH

aluminium amalgam

Rx-ID: 7025292 View in Reaxys 121/141 Yield

Conditions & References Cohen; Recueil des Travaux Chimiques des Pays-Bas; vol. 38; (1919); p. 121 View in Reaxys N

OH N

Rx-ID: 856322 View in Reaxys 122/141 Yield

Conditions & References With hydrogenchloride, ethanol Staudinger; Gaule; Chemische Berichte; vol. 49; (1916); p. 1959 View in Reaxys N

OH N

OH

Cl

H

Rx-ID: 6674324 View in Reaxys 123/141 Yield

Conditions & References Staudinger; Gaule; Chemische Berichte; vol. 49; (1916); p. 1959 View in Reaxys

O

OH

OH

OH

Rx-ID: 373433 View in Reaxys 124/141

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References T= 210 - 220 °C Meerwein; Justus Liebigs Annalen der Chemie; vol. 396; (1913); p. 242; Justus Liebigs Annalen der Chemie; vol. 405; (1914); p. 174 View in Reaxys

OH OH

OH

Rx-ID: 373434 View in Reaxys 125/141 Yield

Conditions & References beim Schmelzen Meerwein; Justus Liebigs Annalen der Chemie; vol. 396; (1913); p. 242; Justus Liebigs Annalen der Chemie; vol. 405; (1914); p. 174 View in Reaxys With potassium hydroxide Meerwein; Justus Liebigs Annalen der Chemie; vol. 396; (1913); p. 242; Justus Liebigs Annalen der Chemie; vol. 405; (1914); p. 174 View in Reaxys

OH

alcoholic KOH-solution OH

O

OH

Rx-ID: 7542380 View in Reaxys 126/141 Yield

Conditions & References Meerwein; Justus Liebigs Annalen der Chemie; vol. 396; (1913); p. 242; Justus Liebigs Annalen der Chemie; vol. 405; (1914); p. 174 View in Reaxys O

OH HO

O

Rx-ID: 22041657 View in Reaxys 127/141

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: alcoholic KOH-solution With potassium hydroxide, diethyl ether Meerwein; Justus Liebigs Annalen der Chemie; vol. 396; (1913); p. 242; Justus Liebigs Annalen der Chemie; vol. 405; (1914); p. 174 View in Reaxys OH

OH

N

Cl

H

tin

NH 2

bis-diphenylen-ethylene O

Rx-ID: 7069859 View in Reaxys 128/141 Yield

Conditions & References Kliegl; Chemische Berichte; vol. 43; (1910); p. 2492 View in Reaxys Schmidt,J.; Stuetzel; Justus Liebigs Annalen der Chemie; vol. 370; (1909); p. 13 View in Reaxys OH

NH 2

Rx-ID: 334340 View in Reaxys 129/141 Yield

Conditions & References With sulfuric acid, sodium nitrite Schmidt; Stuetzel; Justus Liebigs Annalen der Chemie; vol. 370; (1909); p. 16 View in Reaxys OH N

Cl

H

tin

OH

NH 2

compound C26H18O

Rx-ID: 7072454 View in Reaxys 130/141 Yield

Conditions & References Schmidt,J.; Stuetzel; Justus Liebigs Annalen der Chemie; vol. 370; (1909); p. 13

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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View in Reaxys O

OH

Br

sodium amalgam Br

Rx-ID: 7542379 View in Reaxys 131/141 Yield

Conditions & References Montagne; Recueil des Travaux Chimiques des Pays-Bas; vol. 28; (1909); p. 449,453 View in Reaxys O

OH H

H N

zinc dust H

Rx-ID: 7025304 View in Reaxys 132/141 Yield

Conditions & References Werner; Grob; Chemische Berichte; vol. 37; (1904); p. 2895 View in Reaxys O

zinc dust

alcoholic KOH-solution

OH

Rx-ID: 7025306 View in Reaxys 133/141 Yield

Conditions & References Werner; Grob; Chemische Berichte; vol. 37; (1904); p. 2895 View in Reaxys OH

pseudodiphenylene ketone

Rx-ID: 7025301 View in Reaxys 134/141 Yield

Conditions & References With acetic acid, zinc Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys With ethanol, T= 300 °C , im geschlossenen Rohr Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O

OH O

OH

zinc

Rx-ID: 7025307 View in Reaxys 135/141 Yield

Conditions & References Kerp; Chemische Berichte; vol. 29; (1896); p. 230 View in Reaxys

O

OH

O

O

alcoholic potash

O O

Rx-ID: 7156387 View in Reaxys 136/141 Yield

Conditions & References Klinger; Lonnes; Chemische Berichte; vol. 29; (1896); p. 2159 View in Reaxys

barytes solution O O O

O HO

OH

OH

Rx-ID: 5806413 View in Reaxys 137/141 Yield

Conditions & References Anschuetz; Schultz; Justus Liebigs Annalen der Chemie; vol. 196; (1879); p. 48 View in Reaxys

KOH-solution O O

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O

O HO

OH

OH

Rx-ID: 5806414 View in Reaxys 138/141 Yield

Conditions & References Anschuetz; Schultz; Justus Liebigs Annalen der Chemie; vol. 196; (1879); p. 48 View in Reaxys O

O HO

OH N

OH

O

O

O

O

O

Rx-ID: 6674617 View in Reaxys 139/141 Yield

Conditions & References T= 160 °C , im geschlossenen Rohr Friedlaender; Chemische Berichte; vol. 10; (1877); p. 534 View in Reaxys O

OH

sodium amalgam

Rx-ID: 7025303 View in Reaxys 140/141 Yield

Conditions & References Barbier; Annales de Chimie (Cachan, France); vol. <5> 7; (1876); p. 510; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1876); p. 418 View in Reaxys

Cl

air oxygen

cobalt naphthenate

Cl

O

OH

Rx-ID: 6675217 View in Reaxys 141/141 Yield

Conditions & References T= 135 - 145 °C , Dehydrierung I.G. Farbenind.; zit. bei Schenck in K. Ziegler; View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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