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The Regioselectivity of (Dimethylvinylidene)carbene Directed by Aromatic Ring upon the Addition into Aryl Alkenes in the Presence of Other Olefins
Author(s) -
Sheu JyhHorng,
Yen ChingFen,
Huang ChiaWen
Publication year - 1993
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199300010
Subject(s) - chemistry , regioselectivity , carbene , aryl , aromaticity , double bond , conjugated system , ring (chemistry) , cycloaddition , delocalized electron , medicinal chemistry , alkene , electron delocalization , photochemistry , organic chemistry , catalysis , molecule , alkyl , polymer
Abstract Regioselective cycloaddition of (dimethylvinylidene)carbene (1) into aryl alkenes in the presence of other olefins is reported. The reaction is presumably controlled by the phenyl group, which forms an aromatic π‐complex with the carbene C‐3 orbital, followed by the selective addition of 1 to the closest phenyl‐substituted double bond. Also, this selectivity is assumed to be attributed to delocalization of aromatic π electrons which increases the electron density of the conjugated carbon‐carbon double bond, thus leading to the facile addition of vinylidenecarbene.