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The chemistry of sulfenyl halides: Part II: Photochlorination of alkanes with trichloromethylsulfenyl chloride

✍ Scribed by H. Kloosterziel

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 542 KB
Volume: 82
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19630820510

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✦ Synopsis

Abstract

When solutions of trichloromethylsulfenyl chloride, Cl~3~CSCl, in alkanes are exposed to sunlight, alkyl chlorides, hydrogen chloride and hexachlorodimethyl disulfide are formed:

An advantage of this novel chlorination method is the high selectivity, which is even further increased in the presence of benzene. The disulfide may be reconverted to the sulfenyl chloride by molecular chlorine in a separate step.

A radical chain mechanism is proposed for the reaction in which trichloromethylthiyl and alkyl are the chain‐carrying radicals.

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