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

Lookup NU author(s): Parimala Saminathan, Dr Ross Harrington, Emeritus Professor Bill CleggORCiD, Dr Michael HallORCiD

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Abstract

2,2,2-Trichloro-1-aryl-ethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-aryl-ethanones 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-hydroxy-ketones and related molecules.

Publication metadata

Author(s): Essa AH, Lerrick RI, Tuna F, Harrington RW, Clegg W, Hall MJ

Publication type: Article

Publication status: Published

Journal: Chemical Communications

Year: 2013

Volume: 49

Issue: 27

Pages: 2756-2758

Print publication date: 19/02/2013

ISSN (print): 1359-7345

ISSN (electronic): 1364-548X

Publisher: RSC Publications

URL: http://dx.doi.org/10.1039/C3CC39147G

DOI: 10.1039/C3CC39147G

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