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Facile Formation of a Persistent Butadien‐2‐yl Cation Stabilized by Hyperconjugation with an AlC Bond
Author(s) -
Uhl Werner,
Grunenberg Jörg,
Hepp Alexander,
Matar Madhat,
Vinogradov Andrej
Publication year - 2006
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.200504428
Subject(s) - hyperconjugation , chemistry , cationic polymerization , electrophile , hydride , electrophilic addition , medicinal chemistry , atom (system on chip) , photochemistry , double bond , carbon atom , ion , stereochemistry , polymer chemistry , ring (chemistry) , organic chemistry , molecule , catalysis , metal , computer science , embedded system
An aluminating discovery : Hydroalumination of 1,4‐di( tert ‐butyl)butadiyne with di( tert ‐butyl)aluminum hydride affords a persistent butadien‐2‐yl cation (red in scheme). The stabilization of this compound is achieved in particular by hyperconjugation with an AlC bond, and the effective chelating coordination by the aluminum atoms prevents the migration of the hydride ion to the electrophilic cationic carbon atom.