Dynamic path bifurcation in the Beckmann reaction: Support from kinetic analyses

Y Yamamoto, H Hasegawa…

Index: Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4652 - 4660

Full Text: HTML

Citation Number: 31

Abstract

The reactions of oximes to amides, known as the Beckmann rearrangement, may undergo fragmentation to form carbocations+ nitriles when the migrating groups have reasonable stability as cations. The reactions of oxime sulfonates of 1-substituted-phenyl-2-propanone derivatives (7-X) and related substrates (8-X, 9a-X) in aqueous CH3CN gave both rearrangement products (amides) and fragmentation products (alcohols), the ratio of ...

 Related Synthetic Route
1-(3,4-dimethylphenyl)propan-2-one O-naphthalen-2-ylsulfonyl oxime Structure

1309380-84-4

1-(3,4-dimethyl...

~86%

3,4-dimethylbenzyl alcohol Structure

6966-10-5

3,4-dimethylben...

N-[(3,4-dimethylphenyl)methyl]acetamide Structure

65609-15-6

N-[(3,4-dimethy...

Learn More
3-methyl-3-phenylbutan-2-one O-((4-methoxyphenyl)sulfonyl) oxime Structure

1309380-98-0

3-methyl-3-phen...

~%

α-Cumyl alcohol Structure

617-94-7

α-Cumyl alcohol

N-(2-phenylpropan-2-yl)acetamide Structure

79649-68-6

N-(2-phenylprop...

Learn More
3-(m-methylphenyl)-2-butanone oxime Structure

1309381-13-2

3-(m-methylphen...

~%

alpha-3-dimethylbenzyl alcohol Structure

7287-81-2

alpha-3-dimethy...

Learn More
N/A Structure

92916-05-7

N/A

~%

alpha-3-dimethylbenzyl alcohol Structure

7287-81-2

alpha-3-dimethy...

Learn More
3-(m-tolyl)butan-2-one O-naphthalen-2-ylsulfonyl oxime Structure

1309380-91-3

3-(m-tolyl)buta...

~24%

N-(1-(m-methylphenyl)ethyl)acetamide Structure

1070875-05-6

N-(1-(m-methylp...

alpha-3-dimethylbenzyl alcohol Structure

7287-81-2

alpha-3-dimethy...

Learn More
4-(2-(((naphthalen-2-ylsulfonyl)oxy)imino)propyl)benzonitrile Structure

1309380-86-6

4-(2-(((naphtha...

~98%

N-[(4-cyanophenyl)methyl]acetamide Structure

98088-12-1

N-[(4-cyanophen...

Learn More
3-methyl-3-(p-tolyl)butan-2-one O-((4-methoxyphenyl)sulfonyl) oxime Structure

1309380-97-9

3-methyl-3-(p-t...

~97%

2-(4-Methylphenyl)propan-2-ol Structure

1197-01-9

2-(4-Methylphen...

Learn More
1-(4-chlorophenyl)propan-2-one O-naphthalen-2-ylsulfonyl oxime Structure

1262155-46-3

1-(4-chlorophen...

~97%

ACETAMIDE, N-[(4-CHLOROPHENYL)METHYL] Structure

57058-33-0

ACETAMIDE, N-[(...

Learn More
N/A Structure

1262155-45-2

N/A

~92%

p-tolylmethanol Structure

589-18-4

p-tolylmethanol

ACETAMIDE, N-[(4-METHYLPHENYL)METHYL] Structure

25079-96-3

ACETAMIDE, N-[(...

Learn More
1-phenylpropan-2-one O-naphthalen-2-ylsulfonyl oxime Structure

1262155-44-1

1-phenylpropan-...

~99%

n-benzylacetamide Structure

588-46-5

n-benzylacetamide

Learn More
N/A Structure

1309380-96-8

N/A

~99%

2-(4-Methoxyphenyl)-2-propanol Structure

7428-99-1

2-(4-Methoxyphe...

Learn More
1-(4-nitrophenyl)propan-2-one O-naphthalen-2-ylsulfonyl oxime Structure

1309380-87-7

1-(4-nitropheny...

~99%

N-((4-NITROPHENYL)METHYL)ACETAMIDE Structure

56222-10-7

N-((4-NITROPHEN...

Learn More
3-(m,p-dimethylphenyl)-2-butanone oxime Structure

1309381-11-0

3-(m,p-dimethyl...

~%

1-(3,4-Dimethylphenyl)ethanol Structure

33967-19-0

1-(3,4-Dimethyl...

Learn More
3-(3,4-dimethylphenyl)butan-2-one Structure

64394-34-9

3-(3,4-dimethyl...

~%

1-(3,4-Dimethylphenyl)ethanol Structure

33967-19-0

1-(3,4-Dimethyl...

Learn More
3-(3,4-dimethylphenyl)butan-2-one O-naphthalen-2-ylsulfonyl oxime Structure

1309380-89-9

3-(3,4-dimethyl...

~60%

1-(3,4-Dimethylphenyl)ethanol Structure

33967-19-0

1-(3,4-Dimethyl...

N/A Structure

894376-27-3

N/A

Learn More
4-Methoxyphenylacetone Structure

122-84-9

4-Methoxyphenyl...

~%

ACETAMIDE, N-[(4-METHOXYPHENYL)METHYL] Structure

35103-34-5

ACETAMIDE, N-[(...

4-Methoxybenzyl alcohol Structure

105-13-5

4-Methoxybenzyl...

Learn More
1-(4-Methoxyphenyl)acetoneoxime Structure

52271-41-7

1-(4-Methoxyphe...

~%

ACETAMIDE, N-[(4-METHOXYPHENYL)METHYL] Structure

35103-34-5

ACETAMIDE, N-[(...

4-Methoxybenzyl alcohol Structure

105-13-5

4-Methoxybenzyl...

Learn More
1-(4-methoxyphenyl)propan-2-one O-naphthalen-2-ylsulfonyl oxime Structure

1309380-83-3

1-(4-methoxyphe...

~%

ACETAMIDE, N-[(4-METHOXYPHENYL)METHYL] Structure

35103-34-5

ACETAMIDE, N-[(...

4-Methoxybenzyl alcohol Structure

105-13-5

4-Methoxybenzyl...

Learn More
1-(3-Chlorophenyl)acetone Structure

14123-60-5

1-(3-Chlorophen...

~90%

(3-chlorophenyl)acetone oxime Structure

319474-76-5

(3-chlorophenyl...

Learn More

Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2026 ChemSrc All Rights Reserved