The use of polymeric sulfides as catalysts for the para-regioselective chlorination of phenol and 2-chlorophenol

Smith, Keith, Hegazy, Amany S. and El-Hiti, Gamal A. 2019. The use of polymeric sulfides as catalysts for the para-regioselective chlorination of phenol and 2-chlorophenol. Journal of Sulfur Chemistry 41 (1) , pp. 1-12. 10.1080/17415993.2019.1688815

Preview

PDF - Accepted Post-Print Version Download (487kB) | Preview

Abstract

Various poly(alkylene sulfide)s have been synthesized and used as catalysts to enhance the para-regioselectivity in chlorination of phenol and 2-chlorophenol using freshly distilled sulfuryl chloride in the presence of AlCl3 as an activator. Poly(alkylene sulfide)s having alternating spacers, one having three methylene groups and the second having three, six or nine methylene groups were the most para-regioselective catalysts in chlorination of both phenol and 2-chlorophenol. For example, chlorination of phenol and 2-chlorophenol in the presence of optimal examples of such poly(alkylene sulfide)s gave 4-chlorophenol and 2,4-dichlorophenol as the major products in 94.8 and 95.4% yields, respectively, compared with 75.4 and 55.0% yields in the absence of catalysts. In addition, double chlorination of phenol in the presence of poly(alkylene sulfide)s gave 2,4-dichlrophenol in up to 97.1% yield compared with only 58.6% in the absence of catalysts.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry
Publisher:	Taylor & Francis: STM, Behavioural Science and Public Health Titles
ISSN:	1741-5993
Funders:	King Saud University
Date of First Compliant Deposit:	9 January 2020
Date of Acceptance:	30 October 2019
Last Modified:	06 Nov 2023 21:11
URI:	https://orca.cardiff.ac.uk/id/eprint/128394

Citation Data

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

Actions (repository staff only)

Edit Item