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

Literature Information

Publication Date 2018-03-13
DOI 10.1039/C8OB00377G
Impact Factor 3.876
Authors

Konstantin L. Ivanov, Stanislav I. Bezzubov, Mikhail Ya. Melnikov, Ekaterina M. Budynina


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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