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A cautionary note on the use of p-nitrobenzenesulfonamides as protecting groups

โœ Scribed by Peter G.M. Wuts; Jill M. Northuis

Book ID
104259278
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
114 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The cleavage of p-nitrobenzenesulfonamides using thiolate was found to give poor regioselectivity. Cleavage requires addition of thiolate at the sulfonamide carbon, but some addition occurs at the nitro carbon resulting in simple displacement of the nitro group rather than sulfonamide cleavage. The side reaction is most prevalent with cyclic amines and steric effects play only a limited role. This lack of regioselectivity is not observed for o-nitrobenzenesulfonamides.

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