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

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) me...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-02, Vol.47 (7), p.1237-1240
Main Authors: Saltiel, Jack, Bremer, Michael A, Laohhasurayotin, Somchoke, Krishna, Tallapragada S.R
Format: Article
Language:English
Subjects:
dienes
isomerization
one-bond twist
photochemistry
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Summary: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).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200704465