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Unusually Stable Vinyl Cations
Author(s) -
Müller Thomas,
Meyer Rita,
Lennartz Dirk,
Siehl HansUllrich
Publication year - 2000
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 - 10.1002/1521-3773(20000901)39:17<3074::aid-anie3074>3.0.co;2-t
Subject(s) - intramolecular force , silylation , chemistry , ion , polymer chemistry , photochemistry , inorganic chemistry , stereochemistry , organic chemistry , catalysis
Intramolecular addition of transient silylium ions 1 to C≡C bonds provides access to vinyl cations 2 (see scheme; R=Me, Ph) which are remarkably stable at room temperature. The pronounced stabilization of the two cations can be explained by the well‐documented hyperconjugative effect of two β ‐silyl substituents.