Bulletin of the Chemical Society of Japan

Pseudohalogen Chemistry. V. Homolytic Addition of Thiocyanogen Chloride to Some Haloalkenes on Irradiation with UV Light

RG Guy, I Pearson

Index: Guy,R.G.; Pearson,I. Bulletin of the Chemical Society of Japan, 1977 , vol. 50, p. 541 - 542

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Citation Number: 13

Abstract

When irradiated with UV light, thiocyanogen chloride reacts with haloalkenes containing 1–4 halo substituents yielding α-chloro-β-thiocyanato compounds. Addition to unsymmetrical alkenes is regioselectively antiMarkownikov. A radical-chain mechanism, involving SH 2 displacement on the sulfur atom of thiocyanogen chloride and chlorine atoms as the adding/chain-carrying species, is proposed.