Journal of Organic Chemistry p. 1 - 4 (1982)
Update date:2022-08-16
Topics:
Dolbier, William R.
Sellers, Simon F.
The thermal isomerizations of cis- and trans-2,2-difluoro-3-methyl-1-vinylcyclopropane (4 and 5) proceed in a manner reminiscent of the respective hydrocarbon systems. 3,3-Difluoro-1,4-hexadiene (8) is the sole product from 4 while 3,3-difluoro-4-methylcyclopentene (9) is the major product from 5.Both 4, in undergoing its concerted H-shift process, and 5, in rearranging via a diradical process, exhibit the 8-10 kcal/mol incremental activation energy lowering which is expected for reactions involving cleavage of that cyclopropane carbon-carbon bond which is opposite the gem-difluoro substituent.
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