Anodic Cleavage of Several Ketone N-Phenylsemicarbazones into Methyl N-Phenylcarbamate and the Corresponding Dimethyl Acetals

…, K Ohashi, M Okimoto, M Hoshi, T Yoshida

Index: Nishikawa, Shinnosuke; Yamamori, Haruki; Ohashi, Kousuke; Okimoto, Mitsuhiro; Hoshi, Masayuki; Yoshida, Takashi Synthetic Communications, 2013 , vol. 43, # 13 p. 1766 - 1771

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Abstract

Several ketone N-phenylsemicarbazones were electrooxidized in the presence of potassium iodide and a base using methanol as the solvent to give nearly commensurate amounts of methyl N-phenylcarbamate and the corresponding dimethyl acetals. Continuous evolution of gaseous nitrogen was observed from the anolyte during the electrooxidation. The reactions were carried out under very mild reaction conditions and are presumed to proceed through a four- ...

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Hydrazinecarboxamide,N-phenyl Structure

537-47-3

Hydrazinecarbox...

~%

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

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Methanol Structure

67-56-1

Methanol

1-(benzhydrylideneamino)-3-phenylurea Structure

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1-(benzhydrylid...

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Benzene,1,1'-(dimethoxymethylene)bis Structure

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Benzene,1,1'-(d...

Carbamic acid,N-phenyl-,methyl ester Structure

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Methanol Structure

67-56-1

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N/A Structure

21367-50-0

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~63%

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

4,4’-dimethoxybenzophenone dimethyl acetal Structure

2186-93-8

4,4’-dimethoxyb...

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Methanol Structure

67-56-1

Methanol

4,4'-dimethyl-benzophenone 4-phenyl-semicarbazone Structure

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4,4'-dimethyl-b...

~95%

p-Tolyl ketone Structure

611-97-2

p-Tolyl ketone

4,4'-Dimethylbenzophenone dimethyl acetal Structure

86456-47-5

4,4'-Dimethylbe...

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Methanol Structure

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Methanol

acetone N(4)-phenylsemicarbazone Structure

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acetone N(4)-ph...

~86%

Carbamic acid,N-phenyl-,methyl ester Structure

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Methanol Structure

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Methanol

2-(2-methyl-1-phenylpropylidene)-N-phenylhydrazinecarboxamide Structure

316131-52-9

2-(2-methyl-1-p...

~77%

Carbamic acid,N-phenyl-,methyl ester Structure

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(1,1-dimethoxy-2-methylpropyl)benzene Structure

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(1,1-dimethoxy-...

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Methanol Structure

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Methanol

N/A Structure

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~67%

Carbamic acid,N-phenyl-,methyl ester Structure

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Carbamic acid,N...

N/A Structure

1430321-37-1

N/A

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Methanol Structure

67-56-1

Methanol

N-phenyl-2-(1-phenylpentylidene)hydrazinecarboxamide Structure

316137-73-2

N-phenyl-2-(1-p...

~63%

Carbamic acid,N-phenyl-,methyl ester Structure

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Carbamic acid,N...

(1,1-dimethoxypentyl)benzene Structure

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Methanol Structure

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Methanol

N-phenyl-2-(1-(pyridin-3-yl)ethylidene)hydrazinecarboxamide Structure

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Carbamic acid,N-phenyl-,methyl ester Structure

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N/A Structure

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Methanol Structure

67-56-1

Methanol

2-(1-(furan-2-yl)ethylidene)-N-phenylhydrazinecarboxamide Structure

302604-58-6

2-(1-(furan-2-y...

~44%

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

2-acetylfuran dimethoxy acetal Structure

123826-63-1

2-acetylfuran d...

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Methanol Structure

67-56-1

Methanol

N/A Structure

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N/A

~52%

Carbamic acid,N-phenyl-,methyl ester Structure

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Carbamic acid,N...

4,4-dimethoxyheptane Structure

55904-99-9

4,4-dimethoxyheptane

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Methanol Structure

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Methanol

2-(octan-2-ylidene)-N-phenylhydrazinecarboxamide Structure

293325-99-2

2-(octan-2-ylid...

~67%

2,2-dimethoxy octane Structure

54583-19-6

2,2-dimethoxy octane

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

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Methanol Structure

67-56-1

Methanol

4'-Methoxyacetophenon-(4-phenylsemicarbazon) Structure

22454-68-8

4'-Methoxyaceto...

~80%

4'-Methoxyacetophenone dimethyl acetal Structure

27150-99-8

4'-Methoxyaceto...

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

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Methanol Structure

67-56-1

Methanol

N/A Structure

22454-63-3

N/A

~64%

1-chloro-4-(1,1-dimethoxyethyl)benzene Structure

72360-69-1

1-chloro-4-(1,1...

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

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Methanol Structure

67-56-1

Methanol

N/A Structure

21367-49-7

N/A

~49%

1-chloro-4-[(4-chlorophenyl)-dimethoxymethyl]benzene Structure

6861-53-6

1-chloro-4-[(4-...

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

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Methanol Structure

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Methanol

N/A Structure

22454-63-3

N/A

~92%

1-chloro-4-(1,1-dimethoxyethyl)benzene Structure

72360-69-1

1-chloro-4-(1,1...

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

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Methanol Structure

67-56-1

Methanol

N/A Structure

21367-49-7

N/A

~73%

1-chloro-4-[(4-chlorophenyl)-dimethoxymethyl]benzene Structure

6861-53-6

1-chloro-4-[(4-...

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

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Methanol Structure

67-56-1

Methanol

cyclohexanone 4-phenylsemicarbazone Structure

24060-13-7

cyclohexanone 4...

~80%

1,1-Dimethoxycyclohexane Structure

933-40-4

1,1-Dimethoxycy...

Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

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acetone N(4)-phenylsemicarbazone Structure

78002-37-6

acetone N(4)-ph...

~%

1-(benzhydrylideneamino)-3-phenylurea Structure

3043-79-6

1-(benzhydrylid...

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Carbamic acid,N-phenyl-,methyl ester Structure

2603-10-3

Carbamic acid,N...

~%

1-(benzhydrylideneamino)-3-phenylurea Structure

3043-79-6

1-(benzhydrylid...

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Benzophenone Structure

119-61-9

Benzophenone

Hydrazinecarboxamide,N-phenyl Structure

537-47-3

Hydrazinecarbox...

~%

1-(benzhydrylideneamino)-3-phenylurea Structure

3043-79-6

1-(benzhydrylid...

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