1. Alkyl-NH2 to Alkyl-NO2 [Reaxys, Reactions (49); 2016-03-07]

Query Query 1. Query

NH 2 ALK

NO 2 ALK

Results

Date

49 reactions in Reaxys

2016-03-07 12h:32m:19s (EST)

Search as: As drawn, No salts, No mixtures

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O

NH 2

N O

Rx-ID: 684164 View in Reaxys 1/49 Yield

Conditions & References

100 %

With dihydrogen peroxide, Na12[WZn3(H2O)2(ZnW9O34)2], Time= 7h, T= 75 °C Sloboda-Rozner, Dorit; Witte, Peter; Alsters, Paul L.; Neumann, Ronny; Advanced Synthesis and Catalysis; vol.

346; nb. 2-3; (2004); p. 339 - 345 View in Reaxys

78 %

With potassium permanganate in water, 1.) 11 deg C -> room temperature, 8 h, 2.) 55 deg C, 18 h Janzen, Edward G.; Nutter, Dale E.; Magnetic Resonance in Chemistry; vol. 35; nb. 2; (1997); p. 131 - 140 View in Reaxys

76 %

With NaMnO4 in hexane, Time= 24h, T= 69 °C Menger, Fredric M.; Lee, Chuan; Tetrahedron Letters; vol. 22; nb. 18; (1981); p. 1655 - 1656 View in Reaxys

64 %

With tert.-butylhydroperoxide, 3 A molecular sieve, zirconium tetra-t-butoxide in dichloromethane, Time= 5h, T= 22 °C Krohn, Karsten; Kuepke, Jochen; European Journal of Organic Chemistry; nb. 4; (1998); p. 679 - 682 View in Reaxys

61 %

Zhang, Yongkang; Xu, Guangzhi; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 44; nb. 11; (1989); p.

1475 - 1478 View in Reaxys

39 %

Oxidation Jezierski, Adam; Zakrzewski, Jerzy; Moszczyski, Wiesaw; Pesticide Science; vol. 55; nb. 12; (1999); p. 1229 - 1232 View in Reaxys With potassium permanganate, water Kornblum et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 4003 View in Reaxys

90 % Chro- With 3,3-dimethyldioxirane in acetone, Time= 0.5h, Ambient temperature mat.

Murray, Robert W.; Jeyaraman, Ramasubbu; Mohan, Lily; Tetrahedron Letters; vol. 27; nb. 21; (1986); p. 2335 2336 View in Reaxys 100 % Chromat.

With dihydrogen peroxide, methyltrioxorhenium (VII) in ethanol, Time= 2h, Ambient temperature Murray, Robert W.; Iyanar, Kaliappan; Chen, Jianxin; Wearing, James T.; Tetrahedron Letters; vol. 37; nb. 6; (1996); p. 805 - 808 View in Reaxys

NH 2

O N O

Rx-ID: 3307697 View in Reaxys 2/49 Yield 80 %

Conditions & References With tert.-butylhydroperoxide, chromium silicalite-2 in methanol, Time= 5h, T= 65 °C Jayachandran, B.; Sasidharan, M.; Sudalai, A.; Ravindranathan, T.; Journal of the Chemical Society, Chemical Communications; nb. 15; (1995); p. 1523 - 1524 View in Reaxys

80 %

With tert.-butylhydroperoxide, molecular sieve in methanol, Time= 5h, Heating

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Suresh; Joseph; Jayachandran; Pol; Vinod; Sudalai; Sonawane; Ravindranathan; Tetrahedron; vol. 51; nb. 41; (1995); p. 11305 - 11318 View in Reaxys 84 % Chro- With 3,3-dimethyldioxirane in acetone, Time= 0.5h, Ambient temperature mat.

Murray, Robert W.; Jeyaraman, Ramasubbu; Mohan, Lily; Tetrahedron Letters; vol. 27; nb. 21; (1986); p. 2335 2336 View in Reaxys

NH 2

O N O

Rx-ID: 3518819 View in Reaxys 3/49 Yield 80 %

Conditions & References With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 3h, T= 83 °C Vanelle; Crozet; Maldonado; Barreau; European Journal of Medicinal Chemistry; vol. 26; nb. 2; (1991); p. 167 - 178 View in Reaxys

80 %

With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 3h, Heating Vanelle; Madadi; Roubaud; Maldonado; Crozet; Tetrahedron; vol. 47; nb. 28; (1991); p. 5173 - 5184 View in Reaxys With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 3h, Heating Vanelle, Patrice; Benakli, Kamel; Maldonado, Jose; Crozet, Michel P.; Heterocycles; vol. 48; nb. 1; (1998); p. 181 - 185 View in Reaxys With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 3h, Heating Meuche-Albeny; Rathelot; Crozet; Vanelle; Chemistry of Heterocyclic Compounds; vol. 39; nb. 8; (2003); p. 989 997 View in Reaxys NH 2

O N O

Rx-ID: 1831821 View in Reaxys 4/49 Yield 95 %

Conditions & References With water, fluorine in dichloromethane, acetonitrile, Time= 0.5h, T= 20 °C , Inert atmosphere, Flow reactor McPake, Christopher B.; Murray, Christopher B.; Sandford, Graham; ChemSusChem; vol. 5; nb. 2; (2012); p. 312 - 319 View in Reaxys

85 %

With HOF* CH3CN, NAF in dichloromethane, water, acetonitrile, T= -15 °C Rozen, Shlomo; Kol, Moshe; Journal of Organic Chemistry; vol. 57; nb. 28; (1992); p. 7342 - 7344 View in Reaxys

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NH 2

O N O

Rx-ID: 4929434 View in Reaxys 5/49 Yield

Conditions & References

73 %

Stage 1: With ozone in ethyl acetate, T= 25 °C Stage 2: With dihydrogen peroxide in water, T= 25 °C Irfan, Muhammad; Glasnov, Toma N.; Kappe, C. Oliver; Organic Letters; vol. 13; nb. 5; (2011); p. 984 - 987 View in Reaxys

72 %

With tert.-butylhydroperoxide, 3 A molecular sieve, zirconium tetra-t-butoxide in dichloromethane, Time= 5h, T= 22 °C Krohn, Karsten; Kuepke, Jochen; European Journal of Organic Chemistry; nb. 4; (1998); p. 679 - 682 View in Reaxys

NH 2

O N O

Rx-ID: 1908129 View in Reaxys 6/49 Yield 59 %

Conditions & References With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 3h, T= 83 °C Vanelle; Crozet; Maldonado; Barreau; European Journal of Medicinal Chemistry; vol. 26; nb. 2; (1991); p. 167 - 178 View in Reaxys

59 %

With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 3h, Heating Vanelle; Madadi; Roubaud; Maldonado; Crozet; Tetrahedron; vol. 47; nb. 28; (1991); p. 5173 - 5184 View in Reaxys NH 2 O N O

Rx-ID: 4930145 View in Reaxys 7/49 Yield 84 %

Conditions & References With tert.-butylhydroperoxide, 3 A molecular sieve, zirconium tetra-t-butoxide in dichloromethane, Time= 5h, T= 22 °C Krohn, Karsten; Kuepke, Jochen; European Journal of Organic Chemistry; nb. 4; (1998); p. 679 - 682 View in Reaxys O NH 2

N O

Rx-ID: 33165846 View in Reaxys 8/49 Yield 90 %

Conditions & References With water, fluorine in dichloromethane, acetonitrile, Time= 1h, T= 20 °C , Inert atmosphere, Flow reactor McPake, Christopher B.; Murray, Christopher B.; Sandford, Graham; ChemSusChem; vol. 5; nb. 2; (2012); p. 312 - 319 View in Reaxys

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O

NH 2

N O

Rx-ID: 33165847 View in Reaxys 9/49 Yield

Conditions & References

95 %

With water, fluorine in dichloromethane, acetonitrile, Time= 0.5h, T= 20 °C , Inert atmosphere, Flow reactor McPake, Christopher B.; Murray, Christopher B.; Sandford, Graham; ChemSusChem; vol. 5; nb. 2; (2012); p. 312 - 319 View in Reaxys O NH 2

N O

Rx-ID: 33165844 View in Reaxys 10/49 Yield

Conditions & References

80 %

With water, fluorine in acetonitrile, Time= 1h, T= 20 °C , Inert atmosphere, Flow reactor McPake, Christopher B.; Murray, Christopher B.; Sandford, Graham; ChemSusChem; vol. 5; nb. 2; (2012); p. 312 - 319 View in Reaxys 2H

2H 2

H

2 H 2

NH 2H2

H

2

H

2H 2H

2H

O

2H

2

H

N

2H 2H

2H

2H

O

2H 2H

Rx-ID: 2031326 View in Reaxys 11/49 Yield

Conditions & References

46 %

With potassium permanganate in water, Time= 5h, T= 55 °C Haire, D. Lawrence; Janzen, Edward G.; Magnetic Resonance in Chemistry; vol. 32; nb. 3; (1994); p. 151 - 157 View in Reaxys

NH 2

O

O

N

N

N

O

O N O

Rx-ID: 1920104 View in Reaxys 12/49 Yield

Conditions & References

64 %, 13 %, 9 %

With anhydrous potassium sulfate, potassium hydrogensulfate, oxone, sodium hydrogencarbonate in water, acetone Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys

9 %, 13 %, With anhydrous potassium sulfate, potassium hydrogensulfate, oxone, sodium hydrogencarbonate in water, acetone 64 % Crandall, Jack K.; Reix, Thierry; Journal of Organic Chemistry; vol. 57; nb. 25; (1992); p. 6759 - 6764 View in Reaxys

NH 2

O N O

Rx-ID: 129739 View in Reaxys 13/49 Yield

Conditions & References With peracetic acid, 1,2-dichloro-ethane

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Emmons; Journal of the American Chemical Society; vol. 79; (1957); p. 5528 View in Reaxys With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Heating Gilbert,K.E.; Borden,W.T.; Journal of Organic Chemistry; vol. 44; (1979); p. 659 - 661 View in Reaxys 87 % Chro- With 3,3-dimethyldioxirane in acetone, Time= 0.5h, Ambient temperature mat.

Murray, Robert W.; Jeyaraman, Ramasubbu; Mohan, Lily; Tetrahedron Letters; vol. 27; nb. 21; (1986); p. 2335 2336 View in Reaxys

NH 2

O N O

Rx-ID: 215568 View in Reaxys 14/49 Yield

Conditions & References With potassium permanganate, magnesium sulfate, acetone Kornblum et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 4003 View in Reaxys Kornblum; Jones; Organic Syntheses; vol. 43; (1963); p. 87,89 View in Reaxys With tert.-butylhydroperoxide, Time= 16h, T= 110 - 127 °C De La Mare,H.E.; Journal of Organic Chemistry; vol. 25; (1960); p. 2114 - 2126 View in Reaxys O NH 2

N O

Rx-ID: 11191227 View in Reaxys 15/49 Yield

Conditions & References

71 %

With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 0.5h, Heating Gianolio, Eliana; Giovenzana, Giovanni B.; Longo, Dario; Longo, Irene; Menegotto, Ivan; Aime, Silvio; Chemistry - A European Journal; vol. 13; nb. 20; (2007); p. 5785 - 5797 View in Reaxys

O

O

NH 2

NE

N

N O

O

N

O

Rx-ID: 3987709 View in Reaxys 16/49 Yield

Conditions & References

30 % Spectr., 20 % Spectr., 50 % Spectr.

With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline in dichloromethane, Time= 48h, T= 0 °C

5% Spectr., 25 % Spectr., 65 % Spectr.

With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline in dichloromethane, Time= 2h

Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys

Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys

5% With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline in dichloromethane, Time= Spectr., 65 2h

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% Spectr., 25 % Spectr.

NH 2

Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys

O N O

Rx-ID: 210808 View in Reaxys 17/49 Yield

Conditions & References With potassium permanganate, water Kornblum; Clutter; Journal of the American Chemical Society; vol. 76; (1954); p. 4494,4495 View in Reaxys

O

NH 2

N O

Rx-ID: 212911 View in Reaxys 18/49 Yield

Conditions & References With potassium permanganate, magnesium sulfate, acetone Kornblum et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 4003 View in Reaxys

NH 2

O N O

Rx-ID: 213600 View in Reaxys 19/49 Yield

Conditions & References With potassium permanganate, magnesium sulfate, acetone Kornblum et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 4003 View in Reaxys

NH 2

O N

O

EN

N

N

O

O

O

Rx-ID: 3987930 View in Reaxys 20/49 Yield

Conditions & References

15 % Spectr.

With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline in dichloromethane, Time= 48h, T= 20 °C , Yields of byproduct given Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys

NH 2

O

O

N O

N

EN

O

Rx-ID: 956067 View in Reaxys 21/49 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Ambient temperature Gilbert,K.E.; Borden,W.T.; Journal of Organic Chemistry; vol. 44; (1979); p. 659 - 661 View in Reaxys

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O

O NH 2

N

N

O

EN

O

Rx-ID: 1003883 View in Reaxys 22/49 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Heating Gilbert,K.E.; Borden,W.T.; Journal of Organic Chemistry; vol. 44; (1979); p. 659 - 661 View in Reaxys

O NH 2

N O

Rx-ID: 20786871 View in Reaxys 23/49 Yield

Conditions & References Reaction Steps: 2 1: 72 percent / CH2Cl2 / 10 h / 25 °C 2: 85 percent / dimethylsulfoxide / 3 h / 50 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys Reaction Steps: 2 1: 74 percent / 1) NEt3; 2) HOAc / CH2Cl2 / 25 °C / 1) 3h; 2) 5h 2: 60 percent / dimethylsulfoxide / 3 h / 80 °C With acetic acid, triethylamine in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys NH 2

O 15N

O

Rx-ID: 1839690 View in Reaxys 24/49 Yield

Conditions & References With Na15NO2, water, Time= 18h, Ambient temperature, pH 3.5 (5 M HClO4) Brosch, Daniel; Kirmse, Wolfgang; Journal of Organic Chemistry; vol. 58; nb. 5; (1993); p. 1118 - 1121 View in Reaxys

2

H

NH 2

2H

N O

O N

O

O

2H

Rx-ID: 3503324 View in Reaxys 25/49 Yield

Conditions & References With water, sodium nitrite, Time= 18h, Ambient temperature, pH 3.5 (5 M HClO4), Title compound not separated from byproducts Brosch, Daniel; Kirmse, Wolfgang; Journal of Organic Chemistry; vol. 58; nb. 5; (1993); p. 1118 - 1121 View in Reaxys

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O

NH 2

N O

Rx-ID: 20786869 View in Reaxys 26/49 Yield

Conditions & References Reaction Steps: 2 1: 72 percent / CH2Cl2 / 10 h / 25 °C 2: 64 percent / dimethylsulfoxide / 8 h / 60 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys

O N

NH 2

O

Rx-ID: 20786870 View in Reaxys 27/49 Yield

Conditions & References Reaction Steps: 2 1: 72 percent / CH2Cl2 / 10 h / 25 °C 2: 78 percent / dimethylsulfoxide / 5 h / 50 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys NH 2

O N O

Rx-ID: 20786874 View in Reaxys 28/49 Yield

Conditions & References Reaction Steps: 2 1: 70 percent / CH2Cl2 / 12 h / 25 °C 2: 64 percent / dimethylsulfoxide / 9 h / 60 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys NH 2

O N O

Rx-ID: 20786875 View in Reaxys 29/49 Yield

Conditions & References Reaction Steps: 2 1: 70 percent / CH2Cl2 / 12 h / 25 °C 2: 75 percent / dimethylsulfoxide / 5 h / 50 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys

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NH 2

O N O

Rx-ID: 20786876 View in Reaxys 30/49 Yield

Conditions & References Reaction Steps: 2 1: 70 percent / CH2Cl2 / 12 h / 25 °C 2: 86 percent / dimethylsulfoxide / 3 h / 50 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys

O N

NH 2

O

Rx-ID: 20803518 View in Reaxys 31/49 Yield

Conditions & References Reaction Steps: 2 1: 73 percent / CH2Cl2 / 8 h / 25 °C 2: 78 percent / dimethylsulfoxide / 5 h / 50 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys O

NH 2

N O

Rx-ID: 20803519 View in Reaxys 32/49 Yield

Conditions & References Reaction Steps: 2 1: 73 percent / CH2Cl2 / 8 h / 25 °C 2: 63 percent / dimethylsulfoxide / 8 h / 60 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys

O

NH 2

N O

Rx-ID: 20803520 View in Reaxys 33/49 Yield

Conditions & References Reaction Steps: 2 1: 73 percent / CH2Cl2 / 8 h / 25 °C 2: 85 percent / dimethylsulfoxide / 3 h / 50 °C in dichloromethane, dimethyl sulfoxide Katritzky, Alan R.; Kashmiri, M. Akram; Wittmann, Dieter K.; Tetrahedron; vol. 40; nb. 9; (1984); p. 1501 - 1510 View in Reaxys

O 15

NH 2 Cl

H

15N

O

Rx-ID: 9255879 View in Reaxys 34/49

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Yield

Conditions & References With potassium permanganate Saito, Kieko; Yoshioka, Hisashi; Bioscience, Biotechnology and Biochemistry; vol. 66; nb. 10; (2002); p. 2189 - 2193 View in Reaxys O NH 2

N O

Rx-ID: 630391 View in Reaxys 35/49 Yield

Conditions & References With peroxymonosulfuric acid Bamberger; Chemische Berichte; vol. 35; (1902); p. 4294; Chemische Berichte; vol. 36; (1903); p. 711 View in Reaxys O NH 2

N O

Rx-ID: 772774 View in Reaxys 36/49 Yield

Conditions & References With peroxymonosulfuric acid Bamberger; Seligmann; Chemische Berichte; vol. 35; (1902); p. 4299 View in Reaxys

O 15

NH 2

15N

O

Rx-ID: 4476870 View in Reaxys 37/49 Yield

Conditions & References With aq. KMnO7, 1.) 0-5 deg C, 2 h, 2.) 20 deg C, overnight, Yield given Zhang, Yong-Kang; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 51; nb. 1; (1996); p. 139 - 143 View in Reaxys

O

NH 2

N

aqueous potassium permanganate

O

Rx-ID: 5804851 View in Reaxys 38/49 Yield

Conditions & References Kornblum et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 4003 View in Reaxys Kornblum; Clutter; Journal of the American Chemical Society; vol. 76; (1954); p. 4494,4495 View in Reaxys

O

NH 2

O OH

O N O

Rx-ID: 63430 View in Reaxys 39/49 Yield

Conditions & References Emmons; Journal of the American Chemical Society; vol. 79; (1957); p. 5528 View in Reaxys

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O

<2-nitro-1-phenyl-ethyl>-aniline

NH 2

N

H 2N

N O

Rx-ID: 5929979 View in Reaxys 40/49 Yield

Conditions & References Worrall; Journal of the American Chemical Society; vol. 56; (1934); p. 1556,1558 View in Reaxys

-2

NH 2

(v1)

O

O

O

potassium permanganate

Mg2+ (v1)

O

S OO

N O

Rx-ID: 6923844 View in Reaxys 41/49 Yield

Conditions & References Kornblum et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 4003 View in Reaxys -2 (v1)

NH 2

O

O

O

potassium permanganate

Mg2+ (v1)

O

S OO

N O

Rx-ID: 6965396 View in Reaxys 42/49 Yield

Conditions & References Kornblum et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 4003 View in Reaxys

O N O

O

NH 2

HN

N

H 2N

N O

Rx-ID: 635389 View in Reaxys 43/49 Yield

Conditions & References Worrall; Journal of the American Chemical Society; vol. 56; (1934); p. 1556,1558 View in Reaxys

O

NH 2

N O

O

S O

O

N

N

N O

N O

Rx-ID: 3067456 View in Reaxys 44/49 Yield

Conditions & References

65 % in chloroform-d1, Time= 1h, other primary amines, Product distribution Spectr., 30 % Spectr. Zajac, Walter W.; Walters, Thomas R.; Darcy, Michael G.; Journal of Organic Chemistry; vol. 53; nb. 25; (1988); p.

5856 - 5860 View in Reaxys NH 2

O O

N

OH

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O

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O

HO

O

O

N

Rx-ID: 1839680 View in Reaxys 45/49 Yield

Conditions & References With water, sodium nitrite, Time= 18h, Ambient temperature, pH 3.5 (5 M HClO4), Product distribution Brosch, Daniel; Kirmse, Wolfgang; Journal of Organic Chemistry; vol. 58; nb. 5; (1993); p. 1118 - 1121 View in Reaxys

NH 2

sulfomonoperoxoic acid O

tertbutyl-hydroxylamine

N O

O

N

Rx-ID: 6220195 View in Reaxys 46/49 Yield

Conditions & References Bamberger; Seligmann; Chemische Berichte; vol. 36; (1903); p. 703 View in Reaxys

NH 2

sulfomonoperoxoic acid O

O

N O

N

tertpentyl-hydroxylamine Rx-ID: 7087631 View in Reaxys 47/49

Yield

Conditions & References Bamberger; Seligmann; Chemische Berichte; vol. 36; (1903); p. 703 View in Reaxys O NH 2

OH

sulfomonoperoxoic acid

HO

N

N

N H

O

N

O

Rx-ID: 5803426 View in Reaxys 48/49 Yield

Conditions & References Produkt 5:Ameisensaeure Bamberger; Seligmann; Chemische Berichte; vol. 35; (1902); p. 4299 View in Reaxys O NH 2

O

sulfomonoperoxoic acid

N

HO N

H N OH

N

O

Rx-ID: 6045919 View in Reaxys 49/49 Yield

Conditions & References Pr. 5: Essigsaeure Bamberger; Chemische Berichte; vol. 35; (1902); p. 4294; Chemische Berichte; vol. 36; (1903); p. 711 View in Reaxys

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