3. Alkyl=N-OH to Alkyl-NO2 [Reaxys, Reactions (32); 2016-03-07]

Query Query

Results

Date

32 reactions in Reaxys

2016-03-07 12h:13m:52s (EST)

OH

1. Query

N ALK

NO 2 ALK

Search as: As drawn, No salts, No mixtures

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OH N O N O

Rx-ID: 1860945 View in Reaxys 1/32 Yield

Conditions & References

73 %

With disodium hydrogenphosphate, CF3CO3H in acetonitrile, Time= 2h, T= 0 °C Ballini, Roberto; Marcantoni, Enrico; Petrini, Marino; Tetrahedron Letters; vol. 33; nb. 33; (1992); p. 4835 - 4838 View in Reaxys OH N

O N O

Rx-ID: 986525 View in Reaxys 2/32 Yield

Conditions & References

35.6 %

With NaBO3*4H2O in acetic acid, Time= 6.5h, T= 55 °C Durchschein, Katharina; Ferreira-Da Silva, Bianca; Wallner, Silvia; MacHeroux, Peter; Kroutil, Wolfgang; Glueck, Silvia Maria; Faber, Kurt; Green Chemistry; vol. 12; nb. 4; (2010); p. 616 - 619 View in Reaxys (i) Cl2, (ii) O2, O3, (iii) H2, aq. NaOH, Pd-C, Multistep reaction Barnes,M.W.; Patterson,J.M.; Journal of Organic Chemistry; vol. 41; nb. 4; (1976); p. 733 - 735 View in Reaxys OH

H

EN O O

N O

Rx-ID: 5052850 View in Reaxys 3/32 Yield

Conditions & References

70 %

With Oxonereg; in water, acetone, acetonitrile, Time= 6h, T= 45 °C , pH= 7.5, Oxidation Bose, D. Subhas; Vanajatha; Synthetic Communications; vol. 28; nb. 24; (1998); p. 4531 - 4535 View in Reaxys

OH

O

N

N O

Rx-ID: 983666 View in Reaxys 4/32 Yield 33 %

Conditions & References With NaBO3*4H2O in acetic acid, Time= 6.5h, T= 55 °C Durchschein, Katharina; Ferreira-Da Silva, Bianca; Wallner, Silvia; MacHeroux, Peter; Kroutil, Wolfgang; Glueck, Silvia Maria; Faber, Kurt; Green Chemistry; vol. 12; nb. 4; (2010); p. 616 - 619 View in Reaxys (i) Cl2, (ii) O2, O3, (iii) (nBu)3SnH, Multistep reaction Barnes,M.W.; Patterson,J.M.; Journal of Organic Chemistry; vol. 41; nb. 4; (1976); p. 733 - 735 View in Reaxys

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OH

O

N

N O

Rx-ID: 177735 View in Reaxys 5/32 Yield

Conditions & References With N-bromosuccinmide, sodium hydrogencarbonate, Behandeln mit wss.Wasserstoffperoxid und Salpetersaeure und Behandeln des erhaltenen 2-Brom-2-nitro-pentans mit Natriumboranat in Methanol Iffland; Yen; Journal of the American Chemical Society; vol. 76; (1954); p. 4083 View in Reaxys With CF3CO3H, sodium hydrogencarbonate, acetonitrile, Reagens 4:Harnstoff Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys OH N

O N O

Rx-ID: 199859 View in Reaxys 6/32 Yield

Conditions & References With CF3CO3H Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys (i) Cl2, (ii) O2, O3, (iii) H2, aq. NaOH, Pd-C, Multistep reaction Barnes,M.W.; Patterson,J.M.; Journal of Organic Chemistry; vol. 41; nb. 4; (1976); p. 733 - 735 View in Reaxys OH N O N O

Rx-ID: 179079 View in Reaxys 7/32 Yield

Conditions & References With CF3CO3H Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys

OH N

O N O

Rx-ID: 224385 View in Reaxys 8/32 Yield

Conditions & References With N-bromosuccinmide, sodium hydrogencarbonate, Behandeln der Loesung mit wss.Wasserstoffperoxid und Salpetersaeure und Behandeln des Reaktionsprodukts mit Natriumboranat in wss.Methanol Iffland; Yen; Journal of the American Chemical Society; vol. 76; (1954); p. 4083 View in Reaxys

Copyright © 2016 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.

3/9

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OH

F

N

F

O

O N

F

HO

O

O

Rx-ID: 175457 View in Reaxys 9/32 Yield

Conditions & References With sodium hydrogencarbonate, urea, acetonitrile Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys

O

OH F

N

F

N O

O

F

HO O

Rx-ID: 179311 View in Reaxys 10/32 Yield

Conditions & References With urea, acetonitrile Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys

OH

F

N

F

O

F

HO

O N O

O

Rx-ID: 224383 View in Reaxys 11/32 Yield

Conditions & References With sodium hydrogencarbonate, urea, acetonitrile Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys

OH N

H 2N

O

O

N O

NH 2

Rx-ID: 747882 View in Reaxys 12/32 Yield

Conditions & References With CF3CO3H, sodium hydrogencarbonate, acetonitrile Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys OH N O

O

H N Br

N O

Rx-ID: 849859 View in Reaxys 13/32 Yield

Conditions & References With water, zinc oxide, Benhandeln des Reaktionsprodukts mit wss.Wasserstoffperoxid und Salpetersaeure und Behandeln des danach isolierten Reaktionsprodukts mit Natriumboranat in Methanol Iffland; Yen; Journal of the American Chemical Society; vol. 76; (1954); p. 4083 View in Reaxys

Copyright © 2016 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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OH N

O

H N

O

N

Br

O

Rx-ID: 849860 View in Reaxys 14/32 Yield

Conditions & References With water, zinc oxide, Behandlung des Reaktionsprodukts in Petrolaether mit wss.Wasserstoffperoxid und Salpetersaeure und Reduktion des erhaltenen Produkts mit Hilfe von Natriumboranat Iffland; Yen; Journal of the American Chemical Society; vol. 76; (1954); p. 4083 View in Reaxys OH N

O

O

H N

N

Br

O

Rx-ID: 849863 View in Reaxys 15/32 Yield

Conditions & References With water, zinc oxide, beim Behandeln des Reaktionsprodukts mit wss. Wasserstoffperoxid und Salpetersaeure und Behandeln des danach isolierten Reaktionsprodukts mit Natriumboranat in wss. Methanol Iffland; Yen; Journal of the American Chemical Society; vol. 76; (1954); p. 4083 View in Reaxys

OH

O

EN

N O

Rx-ID: 20007062 View in Reaxys 16/32 Yield

Conditions & References Reaction Steps: 3 1: N-bromosuccinimide, sodium bicarbonate / H2O / 3 h 2: 27.9 g / 30percent aq. hydrogen peroxide, conc. nitric acid / 4 h / 50 °C 3: 60 percent / sodium borohydride / methanol; H2O / 12 h With sodium tetrahydroborate, N-bromosuccinmide, dihydrogen peroxide, nitric acid, sodium hydrogencarbonate in methanol, water Haire, D. L.; anzen, Edward G.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1514 - 1522 View in Reaxys

O

OH N

C–

N O N+

Rx-ID: 22772030 View in Reaxys 17/32 Yield

Conditions & References Reaction Steps: 4 1: (i) (chlorination), (ii) (oxidation) 2: (i) H2, aq. NaOH, (ii) NH2OH*HCl 3: aq. NaOH 4: H2O With sodium hydroxide in water Norris,R.K.; Randles,D.; Australian Journal of Chemistry; vol. 32; (1979); p. 2413 - 2422

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View in Reaxys

OH

O

N

N O

Rx-ID: 178181 View in Reaxys 18/32 Yield

Conditions & References /BRN= 1751442/ Iffland; Yen; Journal of the American Chemical Society; vol. 76; (1954); p. 4083 View in Reaxys

OH

O

N

N O

Rx-ID: 22772027 View in Reaxys 19/32 Yield

Conditions & References Reaction Steps: 3 1: (i) (chlorination), (ii) (oxidation) 2: (i) H2, aq. NaOH, (ii) NH2OH*HCl 3: aq. NaOH With sodium hydroxide Norris,R.K.; Randles,D.; Australian Journal of Chemistry; vol. 32; (1979); p. 2413 - 2422 View in Reaxys OH

O

N

N O

Rx-ID: 22776533 View in Reaxys 20/32 Yield

Conditions & References Reaction Steps: 3 1: (i) (chlorination), (ii) (oxidation) 2: (i) H2, aq. NaOH, (ii) NH2OH*HCl 3: aq. NaOH With sodium hydroxide Norris,R.K.; Randles,D.; Australian Journal of Chemistry; vol. 32; (1979); p. 2413 - 2422 View in Reaxys OH N

O N O

Rx-ID: 986520 View in Reaxys 21/32 Yield

Conditions & References (i) Cl2, (ii) O2, O3, (iii) H2, aq. NaOH, Pd-C, Multistep reaction Barnes,M.W.; Patterson,J.M.; Journal of Organic Chemistry; vol. 41; nb. 4; (1976); p. 733 - 735 View in Reaxys

Copyright © 2016 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.

6/9

2016-03-07 12:16:36

OH

O

N

N O

Rx-ID: 986569 View in Reaxys 22/32 Yield

Conditions & References (i) Cl2, (ii) O2, O3, (iii) H2, aq. NaOH, Pd-C, Multistep reaction Barnes,M.W.; Patterson,J.M.; Journal of Organic Chemistry; vol. 41; nb. 4; (1976); p. 733 - 735 View in Reaxys

OH

O

N

N O

Rx-ID: 1017879 View in Reaxys 23/32 Yield

Conditions & References (i) Cl2, (ii) O2, O3, (iii) H2, aq. NaOH, Pd-C, Multistep reaction Barnes,M.W.; Patterson,J.M.; Journal of Organic Chemistry; vol. 41; nb. 4; (1976); p. 733 - 735 View in Reaxys O

OH

O

O

N

N

N

O

O

N

N

E N

O

O

O

OH

O

Rx-ID: 6681511 View in Reaxys 24/32 Yield

Conditions & References T= -60 - 100 °C Boyer; Alul; Journal of the American Chemical Society; vol. 81; (1959); p. 4237 View in Reaxys

OH N

O

N

N O

Rx-ID: 1857066 View in Reaxys 25/32 Yield

Conditions & References With potassium phosphate, glucose-6-phosphate, phenobarbital-induced rat liver microsomes, potassium chloride, nicotinamide adenine dinucleotide phosphate, magnesium chloride, glucose 6-phosphate dehydrogenase, multistep reaction; dehydration of n-butyraldoxime catalyzed by cytochrome P-450, Mechanism DeMaster, Eugene G.; Shirota, Frances N.; Nagasawa, Herbert T.; Journal of Organic Chemistry; vol. 57; nb. 19; (1992); p. 5074 - 5075 View in Reaxys F

OH ZN

F

O

H 2N

O

N

F

HO O

NH 2 O

sodium hydrogencarbonate

N O

Rx-ID: 6923366 View in Reaxys 26/32 Yield

Conditions & References Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys

Copyright © 2016 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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OH N F

F

O

H 2N

O

sodium hydrogencarbonate

N

F

HO

NH 2

O

O N O

Rx-ID: 6923857 View in Reaxys 27/32 Yield

Conditions & References Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys

OH

F

N

O

F

H 2N

O

sodium hydrogencarbonate

N

F

HO

NH 2

O

O N O

Rx-ID: 6961577 View in Reaxys 28/32 Yield

Conditions & References Emmons; Pagano; Journal of the American Chemical Society; vol. 77; (1955); p. 4557 View in Reaxys

OH

O

N

O

sulfomonoperoxoic acid

N

H N OH

O

Rx-ID: 6673298 View in Reaxys 29/32 Yield

Conditions & References Bamberger; Seligman; Chemische Berichte; vol. 35; (1902); p. 3885 View in Reaxys Bamberger; Scheutz; Chemische Berichte; vol. 34; (1901); p. 2027 View in Reaxys

OH

O

N

sulfomonoperoxoic acid

H N

N O

HO O

Rx-ID: 6673478 View in Reaxys 30/32 Yield

Conditions & References Bamberger; Scheutz; Chemische Berichte; vol. 34; (1901); p. 2032 View in Reaxys

OH N

O

H N

sulfomonoperoxoic acid

N

HO

O

O

Rx-ID: 6959853 View in Reaxys 31/32 Yield

Conditions & References Bamberger; Scheutz; Chemische Berichte; vol. 34; (1901); p. 2032 View in Reaxys

Copyright © 2016 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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2016-03-07 12:16:36

OH N

O

H N

sulfomonoperoxoic acid

OH

N O

O

Rx-ID: 7059260 View in Reaxys 32/32 Yield

Conditions & References Bamberger; Scheutz; Chemische Berichte; vol. 34; (1901); p. 2032 View in Reaxys

Copyright © 2016 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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