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Photoisomerization of cis , cis ‐ and cis , trans ‐1,4‐Di‐ o ‐tolyl‐1,3‐butadiene in Glassy Media at 77 K: One‐Bond‐Twist and Bicycle‐Pedal Mechanisms
Author(s) -
Saltiel Jack,
Bremer Michael A.,
Laohhasurayotin Somchoke,
Krishna Tallapragada S. R.
Publication year - 2008
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.200704465
Subject(s) - isomerization , twist , photoisomerization , chemistry , conformational isomerism , isopentane , photochemistry , molecule , catalysis , organic chemistry , geometry , mathematics
Let's twist again : In the isomerization of cis , cis ‐1,4‐di‐ o ‐tolyl‐1,3‐butadiene in isopentane glass at 77 K, hula‐twist pathways are eliminated, because unstable photoproduct conformers do not form. Instead, the isomerization is found to proceed by bicycle‐pedal (BP) and one‐bond‐twist (OBT) mechanisms (see scheme).