e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Organic & biomolecular chemistry

Electrochemical oxidation of amides of type Ph 2 CHCONHAr

T Golub, JY Becker

Index: Golub, Tatiana; Becker, James Y. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 19 p. 3906 - 3912

Full Text: HTML

Citation Number: 10

Abstract

Anodic oxidation of N-aryl-2, 2-diphenylacetamides in acetonitrile undergoes three types of bond-cleavage, one between the benzylic carbon and the carbonyl group, the second between a carbonyl and 'N', and the third between the 'N'atom and aryl group. The selectivity of the cleavage and nature of emerged products is highly dependent on the nature of substituent attached to the aryl group. For example, electron-withdrawing groups direct the ...

N-(4-fluorophenyl)-2,2-diphenylacetamide Structure

N-(4-fluorophen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

Acetanilide, 2,2-diphenyl- Structure

Acetanilide, 2,...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(4'-bromophenyl)-2,2-diphenylacetanilide Structure

N-(4'-bromophen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

Benzeneacetamide,N-(4-methoxyphenyl)-a-phenyl- Structure

Benzeneacetamid...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

Benzeneacetamide,N-(4-chlorophenyl)-a-phenyl- Structure

Benzeneacetamid...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-fluorophenyl)-2,2-diphenylacetamide Structure

N-(4-fluorophen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N/A Structure

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

4-Nitroaniline Structure

~%

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

p-Anisidine Structure

~75%

Benzeneacetamide,N-(4-methoxyphenyl)-a-phenyl- Structure

Benzeneacetamid...

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

N-benzhydrylacetamide Structure

N-benzhydrylace...

N-benzhydrylideneacetamide Structure

N-benzhydrylide...

1-acetyl-3,3-diphenylaziridin-2-one Structure

1-acetyl-3,3-di...

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

N-benzhydrylacetamide Structure

N-benzhydrylace...

N-benzhydrylideneacetamide Structure

N-benzhydrylide...

1-acetyl-3,3-diphenylaziridin-2-one Structure

1-acetyl-3,3-di...

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

Acetanilide, 2,2-diphenyl- Structure

Acetanilide, 2,...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

~%

Benzophenone Structure

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

Benzeneacetamide,N-(4-methoxyphenyl)-a-phenyl- Structure

Benzeneacetamid...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

Benzeneacetamide,N-(4-chlorophenyl)-a-phenyl- Structure

Benzeneacetamid...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-fluorophenyl)-2,2-diphenylacetamide Structure

N-(4-fluorophen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N/A Structure

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4'-bromophenyl)-2,2-diphenylacetanilide Structure

N-(4'-bromophen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

p-Toluidine Structure

~%

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

N-benzhydrylacetamide Structure

N-benzhydrylace...

N-benzhydrylideneacetamide Structure

N-benzhydrylide...

1-acetyl-3,3-diphenylaziridin-2-one Structure

1-acetyl-3,3-di...

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

N-benzhydrylacetamide Structure

N-benzhydrylace...

N-benzhydrylideneacetamide Structure

N-benzhydrylide...

1-acetyl-3,3-diphenylaziridin-2-one Structure

1-acetyl-3,3-di...

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

~%

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

Acetanilide, 2,2-diphenyl- Structure

Acetanilide, 2,...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

~%

Benzophenone Structure

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

N-benzhydrylacetamide Structure

N-benzhydrylace...

Detail

Benzeneacetamide,N-(4-methoxyphenyl)-a-phenyl- Structure

Benzeneacetamid...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

Benzeneacetamide,N-(4-chlorophenyl)-a-phenyl- Structure

Benzeneacetamid...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-fluorophenyl)-2,2-diphenylacetamide Structure

N-(4-fluorophen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N/A Structure

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetonitrile Structure

2,2-Diphenylace...

Detail

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzophenone Structure

Benzeneacetamide, a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

Detail

N-(3-cyanophenyl)-2,2-diphenylacetamide Structure

N-(3-cyanopheny...

~%

Benzeneacetamide,N-(4-chlorophenyl)-a-phenyl- Structure

Benzeneacetamid...

N-(4-methylphenyl)-2,2-diphenyl-acetamide Structure

N-(4-methylphen...

~%

Benzeneacetamide,N-(4-chlorophenyl)-a-phenyl- Structure

Benzeneacetamid...

N-(4-nitrophenyl)-2,2-diphenyl-acetamide Structure

N-(4-nitropheny...

~%

Benzeneacetamide,N-(4-chlorophenyl)-a-phenyl- Structure

Benzeneacetamid...

N-(3-Nitrophenyl)-diphenylacetamid Structure

N-(3-Nitropheny...

~%

Benzeneacetamide,N-(4-chlorophenyl)-a-phenyl- Structure

Benzeneacetamid...

2,2-Diphenylacetic acid Structure

2,2-Diphenylace...

4-Chloroaniline Structure

4-Chloroaniline

~%

Benzeneacetamide,N-(4-chlorophenyl)-a-phenyl- Structure

Benzeneacetamid...

Transfer hydrogenolysis of aryl halides and other hydrogen a...

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Facile and Efficient Amination of Organic Halides Catalyzed ...

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