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Regioselective chlorination of phenols in the presence of tetrahydrothiopyran derivatives

Smith, Keith, Williams, Des and El-Hiti, Gamal A. 2019. Regioselective chlorination of phenols in the presence of tetrahydrothiopyran derivatives. Journal of Sulfur Chemistry 40 (5) , pp. 529-538. 10.1080/17415993.2019.1620230

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Four six-membered cyclic sulfides, namely tetrahydrothiopyran, 3-methyltetrahydrothiopyran, 4-methyltetrahydrothiopyran and 4,4-dimethyltetrahyrdrothiopyran have been used as moderators in chlorination reactions of various phenols with sulfuryl chloride in the presence of aluminum or ferric chloride. On chlorination of phenol, ortho-cresol and meta-cresol the para/ortho chlorination ratios and yields of the para-chloro isomers are higher than when no cyclic sulfide is used for all of the cyclic sulfides, but chlorination of meta-xylenol is less consistent, with some cyclic sulfides producing higher p/o ratios and others producing lower ratios than reactions having no sulfide present.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Taylor & Francis
ISSN: 1741-5993
Date of First Compliant Deposit: 30 May 2019
Date of Acceptance: 11 May 2019
Last Modified: 25 Nov 2020 01:04

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