| Publication Type |
Journal Article |
| Title |
Hydrolysis of aryl N-methyl-N-arylsulfonylcarbamates |
| Authors |
M. Eduarda Araújo M Campelo Jim Iley F Norberto |
| Groups |
HC |
| Journal |
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 |
| Year |
2001 |
| Month |
April |
| Volume |
|
| Number |
4 |
| Pages |
494-497 |
| Abstract |
Tertiary sulfonylcarbamates 1 were prepared by reaction of a sulfonamide anion with aryl chloroformates. These previously unreported compounds hydrolyse in aqueous media to the parent sulfonamide and phenol. The pH-rate profile shows both spontaneous and base-catalysed processes. The reaction is also catalysed by buffers. Kinetic data for the hydrolysis of these compounds by HO- are best interpreted in terms of a mechanism involving rate-limiting formation of a tetrahedral intermediate from nucleophilic attack of hydroxide ion at the carbamate carbonyl carbon atom. For the 4-nitrophenylsulfonyl compound Ih decomposition of the tetrahedral intermediate appears to be rate-limiting with the sulfonamide anion, rather than the phenoxide, functioning as the leaving group. The buffer-catalysed process is consistent with general base-catalysed attack of water at the carbamate carbonyl carbon atom. |
| DOI |
http://dx.doi.org/10.1039/b009146o |
| ISBN |
|
| Publisher |
|
| Book Title |
|
| ISSN |
1472-779X |
| EISSN |
|
| Conference Name |
|
| Bibtex ID |
ISI:000168123900012 |
| Observations |
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