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Cyclopropylallenes III: Stereoselective [1,5] hydrogen migration in cis-1,2,4-cyclodecatriene and cis-bicyclo[7.1.0]deca-2,3-diene

✍ Scribed by David E Minter; G.J Fonken; Frank T Cook

Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 272 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93553-1

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✦ Synopsis

In the course of an ongoing study of the chemistry of substituted cyclopropylidenes, the reactions of gem-dibromocyclopropanes with methyllithium have been used recently in our laboratories to generate a variety of highly strained cyclic allenes.' We report here the syntheses and thermal rearrangements of two particularly interesting examples, each of which is capable of undergoing structural reorganization via cl.51 hydrogen migration. To our knowledge, 1 is the first cyclic, conjugated ene-allene to be isolated and characterized.

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