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The First Persistent β‐Silyl‐Substituted Vinyl Cation
Author(s) -
Siehl Hans Ullrich,
Kaufmann FrankPeter,
Apeloig Yitzhak,
Braude Viviana,
Danovich David,
Berndt Armin,
Stamatis Nikolaos
Publication year - 1991
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.199114791
Subject(s) - hyperconjugation , silylation , chemistry , ab initio , distortion (music) , atom (system on chip) , carbon 13 nmr , computational chemistry , stereochemistry , molecule , organic chemistry , catalysis , materials science , amplifier , optoelectronics , cmos , computer science , embedded system
Stabilized by four β‐silyl groups through hyperconjugation, 1 is the first vinyl cation without π conjugation to be detected by NMR. The 13 C NMR spectrum of 1 at 130 o shows separate signals for the two silyl groups on the methine C atom. Ab initio MO calculations on model systems showed that hyperconjugation controls this hindered rotation, resulting in a preference for a conformation with distortion.
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