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Studies of the Factors Controlling Regioselective Nucleophilic Addition to Dienylium‐Iron Complexes
Author(s) -
Hwang WenShu,
Liao RongLi,
Ong Chi Wi
Publication year - 1988
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.198800012
Subject(s) - chemistry , regioselectivity , nucleophile , steric effects , alkoxy group , medicinal chemistry , counterion , alkyl , ring (chemistry) , electronic effect , nucleophilic addition , stereochemistry , organic chemistry , ion , catalysis
Tricarbonyl(4‐alkoxyl‐1‐alkylcyclohexadienylium)iron complexes (I) react with metal‐cation enolate nucleophiles to give in most cases a mixture of products (II) and (III), resulting from attack at the C‐1 and C‐5 termini of the dienylium ring. Factors that control the regioselectivity of nucleophilic addition, including the steric and electronic effects of the 4‐alkoxyl and 1‐alkyl substituents, the degree of association between the enolate nucleophiles and their counterions, and the polarity of the solvents, were investigated.