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Isomerization of the ( E )‐Alkene of a Conjugated Enyne During Intramolecular Pauson–Khand Cyclization
Author(s) -
Thornton Paul D.,
Burnell D. Jean
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100871
Subject(s) - isomerization , alkene , chemistry , intramolecular force , enyne , conjugated system , alkyne , photochemistry , ene reaction , medicinal chemistry , pauson–khand reaction , stereochemistry , organic chemistry , catalysis , polymer
In the presence of DMSO, the intramolecular Pauson–Khand reactions of two substrates with alkyne moieties substituted by carbon chains consisting of a conjugated ( E )‐alkene and a terminal oxygen function provided cyclized products in which the conjugated alkene underwent E to Z isomerization. This isomerization was consistent with the acceleration of the cyclization process by the terminal oxygen function.