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para-Selective chlorination of cresols and m-xylenol using sulfuryl chloride in the presence of poly(alkylene sulfide)s

Smith, Keith, Hegazy, Amany S. and El-Hiti, Gamal A. 2020. para-Selective chlorination of cresols and m-xylenol using sulfuryl chloride in the presence of poly(alkylene sulfide)s. Journal of Sulfur Chemistry 41 (4) , pp. 345-356. 10.1080/17415993.2020.1740226
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Abstract

Chlorination of o-cresol, m-cresol, and m-xylenol using sulfuryl chloride in the presence of a range of poly(alkylene sulfide)s and a Lewis acid (aluminum or ferric chloride) has been studied. The sulfur containing catalysts used led to the production of para-chlorophenols in high yields and higher para/ortho ratios than for reactions in the absence of such poly(alkylene sulfide)s. The effectiveness of the polymers was found to be dependent on the length of the spacer groups between the sulfur atoms. For example, polymers with shorter spacers provided high yields of 4-chloro-o-cresol (ca. 97%), while polymers with at least one longer spacer provided high yields of both 4-chloro-m-cresol (up to 94.6%) and 4-chloro-m-xylenol (up to 97.6%).

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Taylor & Francis
ISSN: 1741-5993
Date of First Compliant Deposit: 17 March 2020
Date of Acceptance: 4 March 2020
Last Modified: 29 Jun 2020 07:17
URI: http://orca.cf.ac.uk/id/eprint/130443

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