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Reaction of benzyl Grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-?, ?-unsaturated trifluoromethylketones

Coles, S. J., Mellor, J. M., El-Sagheer, A. H. and Salem Eedm Metwally, R. N. (2000) Reaction of benzyl Grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-?, ?-unsaturated trifluoromethylketones Tetrahedron, 56, (51), pp. 10057-10066. (doi:10.1016/S0040-4020(00)00976-5).

Record type: Article

Abstract

Benzyl Grignard reagents react with cyclic ?-alkoxy-?, ? -unsaturated trifluoromethyl ketones by 1,2-addition to afford unsaturated allylic alcohols in high yield. The factors determining the balance between 1,2- and 1,4-addition to unsaturated ketones are discussed. The structures of major and minor products are established by single crystal X-ray diffraction studies.

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More information

Published date: 15 December 2000
Keywords: additions, grignard reagents, trifluoromethylketones ?, ?-unsaturated carbonyl-compounds, ?-enones, ?, ?-ethylenic ketones, regioselectivity, chloride, stereochemistry

Identifiers

Local EPrints ID: 18928
URI: http://eprints.soton.ac.uk/id/eprint/18928
ISSN: 0040-4020
PURE UUID: f8901d9e-7294-4f9e-a1e4-a8ad08ddc629

Catalogue record

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

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Contributors

Author: S. J. Coles
Author: J. M. Mellor
Author: A. H. El-Sagheer
Author: R. N. Salem Eedm Metwally

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