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Control of the Relative Electrophilicity of Alkylating Agents by Variation of the Lewis Acid Concentration
Author(s) -
Mayr Herbert,
Schade Christian,
Rubow Monika,
Schneider Reinhard
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198710291
Subject(s) - lewis acids and bases , carbenium ion , electrophile , chemistry , selectivity , catalysis , carbocation , ionization , lewis acid catalysis , ion , counterion , organic chemistry , computational chemistry , medicinal chemistry
If the carbenium ion of 1 (obtained by ionization) is less stabilized than that of 3, then at least a molar equivalent amount of a completely ionizing Lewis acid is required for the selective formation of 1 : 1 products. If the carbenium ion of 1 is better stabilized than that of 3 , then the highest selectivity for the formation of the 1 : 1 products is achieved with (catalytic amounts) of the weakest Lewis acid possible. These two rules were derived from the results obtained in the reaction of diarylmethyl chlorids with 2‐methyl‐1‐pentene.