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; Ken-ichi Sawa; Katsuyoshi Shibata; Masaki Matsui

doi:10.1055/s-2002-32607

LETTER

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 Sawa^b, Katsuyoshi Shibata^b, 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;

Abstract

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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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References

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