Issue 7, 2013

Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides

Abstract

Benzothiazole-2-sulfonamides react with an excess of hydroxylamine in aqueous solutions to form 2-hydroxybenzothiazole, sulfur dioxide, and the corresponding amine. Mechanistic studies that employ a combination of structure–reactivity relationships, oxygen labeling experiments, and (in)direct detection of intermediates and products reveal that the reaction proceeds via oxygen attack, and that oxygen incorporated in the 2-hydroxybenzothiazole product derives from hydroxylamine. The reaction, which is performed under mild conditions, can be used as a deprotection method for cleavage of benzothiazole-2-sulfonyl-protected amino acids.

Graphical abstract: Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides

Supplementary files

Article information

Article type
Paper
Submitted
01 Oct 2012
Accepted
26 Nov 2012
First published
27 Nov 2012

Org. Biomol. Chem., 2013,11, 1103-1108

Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides

J. J. A. G. Kamps, R. Belle and J. Mecinović, Org. Biomol. Chem., 2013, 11, 1103 DOI: 10.1039/C2OB26929E

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