Cascade dimerization of 2-styryl-1,1-cyclopropanedicarboxylate upon treatment with gallium trichloride


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Abstract

2-Styrylcyclopropane-1,1-dicarboxylate treated with anhydrous gallium trichloride undergoes dimerization with the cyclopropane ring opening and the styryl substituent double bond involvement, leading to the formation of polysubstituted cyclic and bicyclic structures with the predominance of the former or the latter depending on the reaction conditions. Most compounds are formed with very high diastereoselectivity. Thirteen major and minor dimeric structures were isolated and reliably characterized, two of which were found to additionally include a chlorine atom. A rare for the reactions of donor-acceptor cyclopropanes example of the formation of a product with the fused cyclobutane ring was effected at–80 °C. Plausible mechanisms of observed processes were discussed.

About the authors

R. A. Novikov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991

A. V. Tarasova

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991

D. A. Denisov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991

V. A. Korolev

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991

Yu. V. Tomilov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991

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