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Issue 7, 2013
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Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides

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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

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Publication details

The article was received on 01 Oct 2012, accepted on 26 Nov 2012 and first published on 27 Nov 2012


Article type: Paper
DOI: 10.1039/C2OB26929E
Org. Biomol. Chem., 2013,11, 1103-1108

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    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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