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. ORCID: https://orcid.org/0000-0003-0132-0818 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

Preview

PDF - Accepted Post-Print Version Download (514kB) | Preview

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:	20 Nov 2024 04:30
URI:	https://orca.cardiff.ac.uk/id/eprint/113782

Citation Data

Cited 4 times in Scopus. View in Scopus. Powered By Scopus® Data

Actions (repository staff only)

Edit Item