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Issue 27, 2013
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Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: mechanistic investigation and the synthesis of substituted α,α-dichloroketones

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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


Submitted
21 Dec 2012
Accepted
19 Feb 2013
First published
19 Feb 2013

This article is Open Access

Chem. Commun., 2013,49, 2756-2758
Article type
Communication

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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