D. A. Knyazev, M. A. Belaya, A. D. Volodin, A. A. Korlyukov, R. A. Novikov, Yu. V. Tomilov, “Gallium trichloride-mediated reactions of ‘double’ donor–acceptor cyclopropanes with alkenes and dienes”, Mendeleev Commun., 33:1 (2023), 30

Эта публикация цитируется в 3 статьях

Communications

Gallium trichloride-mediated reactions of ‘double’ donor–acceptor cyclopropanes with alkenes and dienes

D. A. Knyazev^a, M. A. Belaya^a, A. D. Volodin^b, A. A. Korlyukov^b, R. A. Novikov^a, Yu. V. Tomilov^a

^a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation

Аннотация: The reactions of ‘double’ donor–acceptor cyclopropanes containing a p- or m-phenylene moiety with alkenes or dienes in the presence of GaCl₃ comprise formation of gallium 1,2-zwitterionic intermediates, the structure of final products being substrate dependent. In contrast to the para-or meta-isomers, reaction of 2,2'-(1,2-phenylene)bis(cyclopropane-1,1-dicarboxylate) does not involve alkene and affords isomeric tricyclo[6.2.2.0^2,7]dodeca-2,4,6-triene-9,9,11,11-tetra-carboxylate, a product of intramolecular rearrangement.

Ключевые слова: ‘double’ donor–acceptor cyclopropanes, gallium trichloride, alkenes, dienes, cycloaddition, annulation, polycyclic carbocycles.

Язык публикации: английский

DOI: 10.1016/j.mencom.2023.01.009

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