Synthetic Routes to, Transformations of, and Rather Surprising Stabilities of (N-Methyl-N-phenylcarbamoyl) sulfenyl Chloride,((N-Methyl-N-phenylcarbamoyl) dithio) …

AM Schrader, AL Schroll, G Barany

Index: Schrader, Alex M.; Schroll, Alayne L.; Barany, George Journal of Organic Chemistry, 2011 , vol. 76, # 19 p. 7882 - 7892

Full Text: HTML

Citation Number: 5

Abstract

The title compound classes,(carbamoyl) sulfenyl chlorides and ((carbamoyl) dithio) carbonyl chlorides, have been implicated previously as unstable, albeit trappable, intermediates in organosulfur chemistry. The present work reports for each of these functional groups:(i) several routes to prepare it in the N-methylaniline family;(ii) its direct structural characterization by several spectroscopic techniques;(iii) its rather unexpected stability ...

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S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

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S-(N-methylanil...

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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(trichloromethyl)(N-methyl-N-phenylcarbamoyl)disulfane Structure

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O-isopropyl N-methyl-N-phenylthiocarbamate Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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O-methyl N-methyl-N-phenylcarbamothioate Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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O-ethyl N-methyl-N-phenylthiocarbamate Structure

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carbaniloyl chloride, n-methyl Structure

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O-ethyl N-methyl-N-phenylthiocarbamate Structure

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(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

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Bis(N-methyl-N-phenylcarbamoyl)disulfane Structure

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Bis(N-methyl-N-...

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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carbaniloyl chl...

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N-methyl-N-trimethylsilylaniline Structure

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O-methyl N-methyl-N-phenylcarbamothioate Structure

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S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

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S-(N-methylanil...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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3-METHYL-2(3H)-...

N-methylaniline,hydrochloride Structure

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(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

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(N-methyl-N-phe...

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O-isopropyl N-methyl-N-phenylthiocarbamate Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

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N-Methylaniline Structure

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N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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O-isopropyl N-methyl-N-phenylthiocarbamate Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl Structure

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N-methyl-N-trimethylsilylaniline Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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O-methyl N-methyl-N-phenylcarbamothioate Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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Chloro(chlorosulfanyl)oxomethane Structure

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O-isopropyl N-methyl-N-phenylthiocarbamate Structure

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N-methyl-N-trimethylsilylaniline Structure

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Chloro(chlorosulfanyl)oxomethane Structure

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S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

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S-(N-methylanil...

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O-ethyl N-methyl-N-phenylthiocarbamate Structure

87463-00-1

O-ethyl N-methy...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

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N-Methylaniline Structure

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monochloroethane Structure

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O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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carbaniloyl chl...

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O-ethyl N-methyl-N-phenylthiocarbamate Structure

87463-00-1

O-ethyl N-methy...

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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Bis(N-methyl-N-phenylcarbamoyl)disulfane Structure

51480-12-7

Bis(N-methyl-N-...

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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O-isopropyl N-methyl-N-phenylthiocarbamate Structure

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3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

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carbaniloyl chloride, n-methyl Structure

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(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

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N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl Structure

4285-42-1

carbaniloyl chl...

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O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl Structure

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N-methyl-N-trimethylsilylaniline Structure

17890-34-5

N-methyl-N-trim...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl Structure

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carbaniloyl chl...

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623-08-5

N,4-Dimethylaniline

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~0%

Structure

1327166-56-2

Detail Learn More
S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

~98%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

N-methylaniline,hydrochloride Structure

2739-12-0

N-methylaniline...

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S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

N-methylaniline,hydrochloride Structure

2739-12-0

N-methylaniline...

(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

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N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

N,4-Dimethylaniline, HCl Structure

2739-05-1

N,4-Dimethylani...

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Benzenamine,N,2,6-trimethyl Structure

767-71-5

Benzenamine,N,2...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

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N/A Structure

1327166-40-4

N/A

Detail Learn More

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