Electrophilic Reactivities of α,β‐Unsaturated Iminium Ions | Zendy

Lakhdar Sami | Zendy; Tokuyasu Takahiro | Zendy; Mayr Herbert | Zendy

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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 .

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