ePrints

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

Lookup NU author(s): Ece Ciftci, Dr Ross Harrington, Dr Paul Waddell, Professor William Clegg, Dr Michael HallORCiD

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.

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

Altmetrics

Funding

Share