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Synthesis of ?,?-unsaturated trifluoromethyl ketones from 4-dimethylamino-1,1,1-trifluorobut-3-ene-2-one by addition of Grignard reagents

Record type: Article

Enaminones are available by reaction of 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one with amines such as dimethylamine and they react with Grignard reagents to give ?, ?-unsaturated trifluoromethyl ketones in good yield by 1,4-addition followed by elimination. The generality of this procedure is contrasted with reactions based either on the use of organolithium nucleophiles, or the use of 4-alkoxy-?, ?-unsaturated trifluoromethyl ketones as electrophilic partners.

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Citation

Andrew, R. J. and Mellor, J. M. (2000) Synthesis of ?,?-unsaturated trifluoromethyl ketones from 4-dimethylamino-1,1,1-trifluorobut-3-ene-2-one by addition of Grignard reagents Tetrahedron, 56, (37), pp. 7261-7266. (doi:10.1016/S0040-4020(00)00597-4).

More information

Published date: 8 September 2000
Keywords: addition, grignard reagents, organolithium, trifluoromethyl-ketones alpha, beta-unsaturated ketones, stereoselective synthesis, efficientsynthesis, enamino ketones, (trifluoromethyl)trimethylsilane, condensation, inhibitors, methyl, esters

Identifiers

Local EPrints ID: 18869
URI: http://eprints.soton.ac.uk/id/eprint/18869
ISSN: 0040-4020
PURE UUID: c3f38059-3509-4592-b0df-07e0df2e947e

Catalogue record

Date deposited: 16 Dec 2005
Last modified: 17 Jul 2017 16:34

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Contributors

Author: R. J. Andrew
Author: J. M. Mellor

University divisions


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