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Cyclopropane Chemistry. Part 4. The Reactions of 1,2,2-Trifluoroethylidene with Alkenes and Pyrolysis of the Resulting Cyclopropanes
Haszeldine, Robert N.,Rowland, Ronald,Speight, James G.,Tipping, Anthony E.
, p. 314 - 324 (2007/10/02)
1,2,2-Trifluoroethylidene, generated by the pyrolysis of (1,1,2,2-tetrafluoroethyl)trifluorosilane, reacts with tetrafluoroethylene, ethylene, and a series of methyl-substituted ethylenes to give the corresponding 1-fluoro-1-difluoromethylcyclopropanes in good yield; cyclohexene gives the corresponding norcarane, and tris(trifluoromethyl)phosphine gives the corresponding phosphorane (CF3)3P(+)-C(-)F-CHF2.Pyrolysis of 1,2,2,3,3-pentafluoro-1-difluoromethylcyclopropane affords difluorocarbene and 3H-pentafluoropropene, but pyrolysis of the methyl-substituted cyclopropanes results in the formation of dienes in high yield, e.g. the 1,4-dienes CHF=CF-CMeR-CMe=CH2 from the cyclopropanes (R = H or Me) or 1,3-dienes from the methyl-substituted cyclopropanes, e.g. --> CH2=CMe-C(CHF2)=CH2.In certain cases further dehydrofluorination of the 1,3-dienes affords trienes, e.g. --> CH2=CMe-C(=CHF)-CMe=CH2.
