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A Remarkable Effect of Silyl Substitution on Electrocyclization of Vinylallenes
Author(s) -
Murakami Masahiro,
Amii Hideki,
Itami Kenichiro,
Ito Yoshihiko
Publication year - 1995
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.199514761
Subject(s) - silylation , substituent , substitution (logic) , chemistry , series (stratigraphy) , kinetics , computational chemistry , stereochemistry , organic chemistry , catalysis , computer science , physics , geology , quantum mechanics , programming language , paleontology
The kinetics and thermodynamics of the electrocyclization of vinylallenes are favorably influenced when a silyl substituent is introduced into the open‐chain compound. A series of vinylallenes containing a silyl group at the vinyl terminus ( 1 ) gave good yields of the corresponding cyclobutenes 2 when heated at reflux in xylene. A theoretical explanation for this observation remains elusive.