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A Silyl Substituent Can Dictate a Concerted Electrocyclic Pathway: Inward Torquoselectivity in the Ring Opening of 3‐Silyl‐1‐cyclobutene
Author(s) -
Murakami Masahiro,
Miyamoto Yasufumi,
Ito Yoshihiko
Publication year - 2001
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(20010105)40:1<189::aid-anie189>3.0.co;2-l
Subject(s) - substituent , cyclobutene , conrotatory and disrotatory , ring (chemistry) , silylation , chemistry , stereochemistry , organic chemistry , catalysis
A preference for inward over outward rotation is found for the thermal conrotatory ring‐opening reaction of 1‐cyclobutene 1 , to produce 1,3‐butadiene 2 , when a silyl substituent is located at the 3‐position. This preference exists in spite of the bulkiness of the substituent.