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Donor–acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes

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Abstract

A new type of donor–acceptor cyclopropane reactivity towards alkenes was revealed for 2-arylcyclopropane-1,1-diesters that contain an OH-group in the ortho-position of the aryl substituent. In this case, the initial cyclopropanes participate in formal (4 + 2)-cycloaddition as synthetic equivalents of ortho-quinone methides which are potential intermediates generated under mild conditions in the presence of a Lewis acid.

Graphical abstract: Donor–acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes

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Publication details

The article was received on 12 Feb 2018, accepted on 13 Mar 2018 and first published on 13 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00377G
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Donor–acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes

    K. L. Ivanov, S. I. Bezzubov, M. Ya. Melnikov and E. M. Budynina, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00377G

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