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Aromatic polyfluoro-compounds—XLV:The reactions of octafluorostyrene

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
25
Issue
7
Identifiers
DOI: 10.1016/s0040-4020(01)82732-0

Abstract

Abstract Octafluorostyrene with bromine and hydrogen bromide in the presence of UV light yielded α,β-dibromooctafluoroethylbenzene and β-bromo-α,β,β,2,3,4,5,6-octafluoroethylbenzene respectively. With dimethylamine, N,N-dimethylpentafluorophenylfluoroacetamide was obtained arising via N,N-dimethyl-α,β,β,2,3,4,5,6-octafluorophenylethylamine The structure of the acetamide was established by NMR spectroscopy, analysis and hydrolysis to pentafluorobenzoic acid and pentafluorophenylfluoro acetic acid. With methanol, octafluorostyrene gave β-methoxy-α,β,β,2,3,4,5,6-octafluoroethylbenzene, and 4-methoxyheptafluorostyrene (established by oxidation of the reaction mixture to yield p-methoxytetrafluorobenzoic acid). Reduction of octafluorostyrene with LAH gave a four component mixture of the cis and trans isomers of α,β,2,3,4,5,6-heptafluorostyrene and α,β,2,3,5,6-hexafluorostyrene.

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