Heats of Hydrogenation, III. Influence of Fluoro Substituents on the Thermal Rearrangement of Cyclopropane Systems
The influence of the fluoro substituents on the isomerisation of 1,1-difluoro-2-vinylcyclopropane (1) and of cis-1,1-difluoro-2-methyl-3-vinylcyclopropane (11) is demonstrated by kinetic methods and by heat of hydrogenation measurements to be a ground state effect (destabilisation of the cyclopropane by 12 - 14 kcal/mol).The transition states of the vinylcyclopropane rearrangement of 1 and of the 1,5-homodienyl hydrogen shift of 11 are more or less effected, depending on their cyclopropane character.
Roth, Wolfgang R.,Kirmse, Wolfgang,Hoffmann, Wilfried,Lennartz, Hans-Werner
p. 2508 - 2515
(2007/10/02)
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