Hydrolysis of aryl N-methyl-N-arenesulfonylcarbamates

Araújo, M. Eduarda M.; Campelo, Margarida; Iley, Jim and Norberto, Fatima (2001). Hydrolysis of aryl N-methyl-N-arenesulfonylcarbamates. Journal of the Chemical Society: Perkin Transactions 2 pp. 494–497.

DOI: https://doi.org/10.1039/b009146o


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 1h 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.

Viewing alternatives


Public Attention

Altmetrics from Altmetric

Number of Citations

Citations from Dimensions
No digital document available to download for this item

Item Actions