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

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

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 o...

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Veröffentlicht in:Organic & biomolecular chemistry 2018, Vol.16 (21), p.3897-3909
Hauptverfasser: Ivanov, Konstantin L, Bezzubov, Stanislav I, Melnikov, Mikhail Ya, Budynina, Ekaterina M
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes
Aromatic compounds
Cycloaddition
Cyclopropane
Diesters
Equivalence
Intermediates
Lewis acid
Organic compounds
Quinones
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container_issue 21
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container_title Organic & biomolecular chemistry
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creator Ivanov, Konstantin L
Bezzubov, Stanislav I
Melnikov, Mikhail Ya
Budynina, Ekaterina M
description 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.
doi_str_mv 10.1039/c8ob00377g
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Alkenes
Aromatic compounds
Cycloaddition
Cyclopropane
Diesters
Equivalence
Intermediates
Lewis acid
Organic compounds
Quinones
title Donor-acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes
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