Fluoro-olefin chemistry. Part IX. Thermal insertion of hexafluoropropene into carbon–hydrogen bonds in alkylbenzenes
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 517-525
- https://doi.org/10.1039/p19760000517
Abstract
The thermal reactions (ca. 250 °C) of the alkylbenzenes ArCH2R (Ar = Ph, R = H, Me, or Et; Ar =p-ClC6H4, R = H; Ar =p-MeC6H4, R = H) with hexafluoropropene give mainly the 1 : 1 adducts ArCHR·CF2·CHF·CF3, together with smaller amounts of the 1 : 1 adducts ArCHR·CF(CF3)·CHF2, 1-alkyl-2,2,3-trifluoro-3-trifluoromethylindanes, 1-alkyl-2,3,3-trifluoro-2-trifluoromethylindanes, and minor amounts of other products. Reaction at high pressure (autoclaves) favours 1 : 1 adduct formation whereas at lower pressure (tubes) indane formation is favoured. The reaction with cumene does not afford 1 : 1 adducts, the major products being 1,2,2,2-tetrafluoroethylbenzene, 1,1-difluoro-2-methylpropene, and the cyclobutane, [graphic omitted]F2; indanes are also formed in this reaction. Chlorination, bromination, and nitration of the 1 : 1 adduct PhCH2·CF2·CHF·CF3 gives the corresponding ortho- and para-substituted derivatives in the ratios 47 : 53, 20 : 80, and 0 : 100, respectively.Keywords
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