Issue 27, 2013
From the journal:

Chemical Communications

Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: mechanistic investigation and the synthesis of substituted α,α-dichloroketones†

Ali H. Essa,ab   Reinner I. Lerrick,ac   Floriana Tuna,d   Ross W. Harrington,a   William Clegga  and  Michael J. Hall*a  

* Corresponding authors

a School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, UK
E-mail: m.hall@ncl.ac.uk
Fax: +44 (0)191 222 6929
Tel: +44 (0)191 222 7321

b Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq

c School of Chemistry, Nusa Cendana University, Indonesia

d School of Chemistry and Photon Science Institute, The University of Manchester, Oxford Road, Manchester, UK

Abstract

2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted α,α-dichloro-β-hydroxyketones and related molecules.

Graphical abstract: Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: mechanistic investigation and the synthesis of substituted α,α-dichloroketones

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Article information

DOI
https://doi.org/10.1039/C3CC39147G
Article type
Communication
Submitted
21 Dec 2012
Accepted
19 Feb 2013
First published
19 Feb 2013
This article is Open Access

Chem. Commun., 2013,49, 2756-2758

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Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: mechanistic investigation and the synthesis of substituted α,α-dichloroketones

A. H. Essa, R. I. Lerrick, F. Tuna, R. W. Harrington, W. Clegg and M. J. Hall, Chem. Commun., 2013, 49, 2756 DOI: 10.1039/C3CC39147G

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