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

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Title:	Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides
Author(s):	Kamps, J.A.G.; Belle, R.; Mecinovic, J.
Publication year:	2013
Source:	Organic & Biomolecular Chemistry, vol. 11, iss. 7, (2013), pp. 1103-1108
ISSN:	1477-0520
DOI:	http://dx.doi.org/10.1039/c2ob26929e
Publication type:	Article / Letter to editor
Please use this identifier to cite or link to this item : http://hdl.handle.net/2066/111518
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Subject:	Synthetic Organic Chemistry
Organization:	Synthetic Organic Chemistry
Journal title:	Organic & Biomolecular Chemistry
Volume:	vol. 11
Issue:	iss. 7
Page start:	p. 1103
Page end:	p. 1108
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.