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Regioselective synthesis of important chlorophenols in the presence of methylthioalkanes with remote SMe, OMe or OH substituents

Smith, Keith, Al-Zuhairi, Ali J., Elliott, Mark C. and El-Hiti, Gamal A. 2018. Regioselective synthesis of important chlorophenols in the presence of methylthioalkanes with remote SMe, OMe or OH substituents. Journal of Sulfur Chemistry 39 (6) , pp. 607-621. 10.1080/17415993.2018.1493111

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Abstract

Various methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes have been used as regioselectivity modifiers in the chlorination reactions of various phenols at room temperature. The process involves the use of a slight excess of sulfuryl chloride in the presence of aluminum or ferric chloride as an activator. Methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes having 2 and 3 methylene groups as a spacer were found to be good for the para-selective chlorination of o-cresol and phenol. On the other hand, methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes having 6 and 9 methylene groups were found to be good for the selective para-chlorination of m-xylenol and m-cresol. Calculations using density functional theory on bis(methylthio)alkanes have suggested two different types of stable chlorinated intermediates depending on the number of methylene units as a spacer.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Taylor & Francis
ISSN: 1741-5993
Date of First Compliant Deposit: 31 July 2018
Date of Acceptance: 12 June 2018
Last Modified: 17 Oct 2019 19:35
URI: http://orca.cf.ac.uk/id/eprint/113782

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