Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides
Publication year
2013Source
Organic & Biomolecular Chemistry, 11, 7, (2013), pp. 1103-1108ISSN
Publication type
Article / Letter to editor

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Organization
Synthetic Organic Chemistry
Journal title
Organic & Biomolecular Chemistry
Volume
vol. 11
Issue
iss. 7
Page start
p. 1103
Page end
p. 1108
Subject
Synthetic Organic ChemistryAbstract
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.
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- Academic publications [205104]
- Faculty of Science [32347]
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