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Electrophilic Reactivities of α,β‐Unsaturated Iminium Ions
Author(s) -
Lakhdar Sami,
Tokuyasu Takahiro,
Mayr Herbert
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802889
Subject(s) - iminium , electrophile , nucleophile , ketene , ion , chemistry , nucleophilic addition , computational chemistry , computer science , medicinal chemistry , organic chemistry , catalysis
How fast do nucleophiles add to iminium ions? Kinetic studies of the reactions of seven iminium ions 1 with cyclic ketene acetals 2 rendered electrophilicity parameters E for these iminium ions. Because N and s parameters are known for numerous nucleophiles, the correlation log k (20 °C)= s ( N + E ) makes it possible to calculate rate constants for nucleophilic attack at the iminium ions 1 .