The reaction of 2-chlorocycloalkanones with vinylmagnesium chloride gives 1,2-divinylcycloalkanols. Divinylation proceeds via a rearrangement of initially formed 2-chloro-1-vinylcycloalkanols to 2-vinylcycloalkanones followed by further vinylation of 2-vinylcycloalkanones. Thermal sigmatropic rearrangement of 1,2-divinylcycloalkanols gives 5-cycloalken-1-ones in good yields. The influence of the size of rings on the reaction pathways is discussed.
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Kato et al. (1980) studied this question.
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