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
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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: | 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 |
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