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Synlett 2002(7): 1134-1136
DOI: 10.1055/s-2002-32607
LETTER
© Georg Thieme Verlag Stuttgart · New York

CFC- or HFC-Free Approach to α-Substituted β,γ,γ-Trifluoroallyl Alcohols by the Reaction of β-Fluoro-β-trifluoromethylated Enol Tosylate with Grignard Reagents

Kazumasa Funabiki*a, Ken-ichi Sawab, Katsuyoshi Shibatab, Masaki Matsui*a
a Department of Materials Science and Technology, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
b Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
Fax: +81(58)2301893; e-Mail: kfunabik@apchem.gifu-u.ac.jp;
Further Information

Publication History

Received 15 April 2002
Publication Date:
07 February 2007 (online)

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Abstract

The reaction of β-fluoro-β-trifluoromethylated enol tosylate with Grignard reagents giving the corresponding β,γ,γ-tri­fluoroallyl alcohols as well as heteropoly acid-mediated ethanolysis of the allyl alcohols affording (Z)-β-substituted α-fluoro-α,β-un­saturated esters is described.

Key words

fluorine - trifluoromethyl - Grignard reaction - sulfonates - cleavage - nucleophilic additions - alcohols - esters

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