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CYCLOPROPANATION OF ARENO-CONDENSED 4H-PYRANS WITH DIHALOCARBENES

Ирина А. Семенова, Виталий А. Осянин, Максим Р. Демидов, Дмитрий В. Осипов, Юрий Н. Климочкин
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Abstract


The addition of dihalocarbenes to 1H-benzo[f]chromenes and 4H-chromenes gave a number of dihalotetrahydro(benzo)cyclopropa[b]chromenes containing donor and acceptor substituents at different positions. It was found that in the case of 1,3-disubstituted 1H-benzo[f]chromenes, the reaction proceeds diastereoselectively with the formation of trans-isomers. 12H,13H-7a,12a-Methanobenzo[f]indeno[1,2-b]chromene and 12,13-dihydro-14H-7a,13a-methanodibenzo[a,h]xanthene, representatives of new heterocyclic systems, were obtained.

Keywords


1H-benzo[f]chromenes; dihalocarbenes; gem-dihalocyclopropanes; tetrahydrocyclo(benzo)propa[b]chromenes; [2+1] cycloaddition.

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