Reaction of benzyl Grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-α, β-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-α, β-unsaturated trifluoromethylketones. Tetrahedron, 56, (51), 10057-10066. (doi:10.1016/S0040-4020(00)00976-5).

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Description/Abstract

Benzyl Grignard reagents react with cyclic β-alkoxy-α, β -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.

Item Type: Article
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Keywords: additions, grignard reagents, trifluoromethylketones α, β-unsaturated carbonyl-compounds, α-enones, α, β-ethylenic ketones, regioselectivity, chloride, stereochemistry
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 18928
Date Deposited: 16 Dec 2005
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/18928

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