Reactions of sodium cyanoborohydride with benzothiazolium and Δ2-thiazolinium cations. Formation of benzothiazolines, thiazolidines and stable thiazaboroles

Harjit Singh, ; Sarin, Rakesh ; Singh, Kamaljit ; Contreras, Rosalinda ; Uribe, Guillermo (1989) Reactions of sodium cyanoborohydride with benzothiazolium and Δ2-thiazolinium cations. Formation of benzothiazolines, thiazolidines and stable thiazaboroles Tetrahedron, 45 (16). pp. 5193-5202. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)81096-6

Abstract

Sodium cyanoborohydride reduction of benzothiazolium 1- and Δ2-thiazolinium 2- cations give benzothiazolines 3- and thiazolidines 5- along with [[ o--(disubstituted amino) phenyl] and 2-(dialkylamino)ethyl]thio]boranecarbonitriles ( N--B- ) 4- and 6-. Because of the heterocyclic structures formed through N→ B coordination and consequent chirality, the latter species constitute mixtures of two diastereomers which are exceptionally stable to acid and base.

Item Type:Article
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Deposited On:12 Nov 2010 13:39
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