The rearrangement yields substituted bromoalkenes in gem-dibromocyclopropanes, suggesting the method's utility in organic synthesis.
It was found for the first time that 2,3-dialkyl-substituted gem-dibromocyclopropanes react with a solution of aluminum carbenoid MeAlCHI in CHCl to give substituted bromoalkenes in good yield. The reaction is sensitive both to the nature of the organoaluminum Lewis acid and to the nature of the substitution of gem-dibromocyclopropane. A theoretical cyclopropyl-allyl rearrangement has been developed. The B3LYP/6-31G(d) method was used to calculate the free activation energies of the cyclopropyl-allyl rearrangement step for a number of gem-dibromocyclopropanes and aluminum-containing Lewis acids.
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A. V. Yaroslavova (2025) studied this question.
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