Triorganotin hydride reduction of 6β-isothiocyanatopenicillanates: a radical-induced sulphur–C(2) bond cleavage
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 17,p. 901-902
- https://doi.org/10.1039/c39810000901
Abstract
Triorganotin hydride reduction of methyl 6β-isothiocyanatopenicillanate is accompanied by intra-molecular radical capture and cleavage of the sulphur–C(2) bond to give thiazolines (9) and (10); a similar mechanism is proposed for the formation of thiazoline (3), a minor product of tri-n-butyltin hydride reduction of benzyl 6α-(1-hydroxyl-1-methylethyl)-6β-isocyanopenicillanate (1; R2= Me2COH).Keywords
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