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The thermal rearrangements of 1,1,2,2,4,4-hexafluorospiropentane and perfluorospiropentane

✍ Scribed by William R. Dolbier Jr.; Simon F. Sellers; Bruce E. Smart

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
196 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

The title compounds were synthesized via CF2: addition to the respective methylenecyclopropanes.

The hexafluorospiropentane thermally rearranges to 2,2,4,4-tetrafluoro-l-(difluoromethyiene)cyclobutane in competition with CF2: extrusion, whereas perfluorospiropentane decomposes exclusively by CF2: extrusion.

Upon thermolysis, gem-difluorocyclopropanes decompose by two competitive pathways:

bond homolysis, usually leading to rearrangement, and difluorocarbene extrusion. 1,2

In no group of compounds are the factors which determine the relative facility with which these two processes compete so well demonstrated as in the fluorinated spiropentanes.

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