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Cyclopropene Chemistry. Part 1. Preparation and Some Reactions of 3,3-Dichloro-1,2-bistrifluoromethyl- and 1,3-Dichloro-2,3-bistrifluoromethyl-cyclopropene
Birchall, J. Michael,Burger, Klaus,Haszeldine, Robert N.,Nona, Shmaiel N.
, p. 2080 - 2086 (1981)
Both the title compounds may be obtained from the reaction of dichlorocarbene with hexafluorobut-2-yne; the 3,3-dichloro-compound is isomerised to the 1,3-dichloro-isomer by heat, light, or chemical catalysis, but conditions are described for the preparation of either pure cyclopropene.Treatment of either isomer with antimony pentafluoride gives solutions containing the chlorobistrifluoromethylcyclopropenium ion.Both isomers undergo free-radical addition of halogens, but the slow reaction of the 1,3-dichloro-compound with trifluoromethyl radicals gives a mixture of products.Diels-Alder reactions of both cyclopropenes with cyclopentadiene or with furan are described, and the 3,3-dichloro-compound gives a high yield of 'ene'-reaction products with (E)-but-2-ene.
