Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Preparation and Cycloaddition Reactions of Pentafluoro-1,3-pentadienes
Hiroshige MuramatsuKan InukaiTeruo Ueda
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1968 Volume 41 Issue 9 Pages 2129-2134

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Abstract

3,4,5,5,5-Pentafluoro-1,3-pentadienes were prepared from 1 : 1 adducts of perfluoropropylene and alcohols by dehydration followed by dehydrofluorination. When 2-methyl-3,4,5,5,5-pentafluoro-1,3-pentadiene was heated at 130–220°C, an intramolecular cyclization occurred to give 1-methyl-2,3-difluoro-3-trifluoromethylcyclobutene in 73–87% yields. α-Trifluoromethyl-β-acetylacrylic acid and 1-trifluoromethyl-2-fluoro-3-methylenecyclobutene were synthesized from the cyclobutene by oxidation and dehydrofluorination, respectively. Several polyfluorocyclobutanes with a perfluoropropenyl group were prepared by the cross-cycloaddition of the pentafluoro-1,3-pentadienes with the fluoroolefins such as 1,1-difluoro-2,2-dichloroethylene, trifluorochloroethylene, and perfluoropropylene.

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