Fluoro-olefin chemistry. Part 17. Thermal reaction of hexafluoropropene with 2-trifluoromethylbutane and 1,1,1-trifluoropentane
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1353-1356
- https://doi.org/10.1039/p19830001353
Abstract
Reaction of hexafluoropropene with 2-trifluoromethylbutane (1) and 1,1,1-trifluoropentane (2) in the range 260–295 °C gives as major products the 1:1 adducts CF3CHMeCH2CH2CF2CHFCF3(10) and CF3CH2CH2CHMeCF2CHFCF3(14), respectively, formed via hydrogen abstraction from C–H bonds γ to the CF3 group. However, dehydrogenation to give 1H,2H-hexafluoropropane (6) and the alkenes CF3CMe:CHMe (7)[from (1)] and CF3CH2CH2CH:CH2(22)[from (2)] is a competing reaction which is more important the higher the temperature. The alkene (7) reacts further to give CF3CMe:CHCH2CF2-CHFCF3(9) and the cyclopentane CF3[graphic omitted]FCF3(18) while the alkene (22) undergoes cyclodimerisation with hexafluoropropene to afford CF3[graphic omitted]HCH2CH2CF3(11) and then the dehydrogenation product CF3[graphic omitted]HCH:CHCF3(13). A further product from the alkane (2) is the olefin CF3CH:CHCH2CH2CF2CHFCF3(12) formed via hydrogen abstraction from a δ-C–H bond. Reaction does not occur between 1,1,1-trifluoro-4-trifluoromethylpentane and hexafluoropropene at 295 °C.Keywords
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