Cyclopropyl-allyl rearrangement gem-dibromocyclopropanes under the action of aluminum carbenoides

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Abstract

It was found for the first time that 2,3-dialkyl-substituted gem-dibromocyclopropanes react with a solution of aluminum carbenoid Me2AlCH2I in CH2Cl2 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.

About the authors

A. V. Yaroslavova

Institute of Petrochemistry and Catalysis of Russian Academy of Sciences

prosp. Oktyabrya, 141, Ufa, 450075 Russia

T. P. Zosim

Institute of Petrochemistry and Catalysis of Russian Academy of Sciences

Email: tania-ygnty@yandex.ru
prosp. Oktyabrya, 141, Ufa, 450075 Russia

I. R. Ramazanov

Institute of Petrochemistry and Catalysis of Russian Academy of Sciences

prosp. Oktyabrya, 141, Ufa, 450075 Russia

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