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Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones

Lookup NU author(s): Ece Ciftci, Dr Ross Harrington, Dr Paul Waddell, Emeritus Professor Bill CleggORCiD, Dr Michael HallORCiD

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Abstract

2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro- 1-arylethen-1-olates and trapped with a range of electrophiles resulting in either reduction, reduction/aldol, reduction/Claisen condensation or reduction/aldol-Tishchenko products. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations, which can be followed by a thermal rearrangement as a route to 1,3- diaryl-3-chloropropane-1,2-diones.

Publication metadata

Author(s): Essa AH, Lerrick RI, Çiftçi E, Harrington RW, Waddell PG, Clegg W, Hall MJ

Publication type: Article

Publication status: Published

Journal: Organic & Biomolecular Chemistry

Year: 2015

Volume: 13

Issue: 20

Pages: 5793-5803

Print publication date: 28/05/2015

Online publication date: 16/04/2015

Acceptance date: 16/04/2015

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: RSC Publications

URL: http://dx.doi.org/10.1039/C5OB00541H

DOI: 10.1039/C5OB00541H

Notes: ASAP

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