Solid state behaviour of vinyl quinones

Article abstract of DOI:10.1080/10587259608039394

2,5-Bisvinyl-1,4-benzoquinones 1 and 2-vinyl-1,4-benzoquinones 2 substituted with aryl or ester end groups have been synthesized. The 2,5-bisstyryl-1,4-benzoquinones 1 (R=phenyl, p-tolyl, o-tolyl) crystallize with a 7 angstrom-stacking axis. But only for the o-tolyl derivative the contacts between the vinyl groups are close enough to allow a four-center type photopolymerization. The ester derivative 1 (R=COOEt) has a layer structure and can be photooligomerized in the crystal. The generated cyclobutane subgroups have twofold symmetry. The vinylquinones 2 (R=aryl) may be dimerized photochemically in the crystal at the vinyl groups to centrosymmetric cyclobutanes. Crystals with 4 angstrom stacking axis are also photoreactive.

Full text of DOI:10.1080/10587259608039394

This article was downloaded by: [Michigan State University]
On: 27 January 2015, At: 17:54
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Molecular Crystals and Liquid Crystals
Science and Technology. Section A.
Molecular Crystals and Liquid Crystals
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/gmcl19
Solid State Behaviour of Vinyl Quinones
Hermann Irngartinger a , Jochen Lichtenthäler a , Rüdiger Herpich a
& Birgit Stadler a
a Institute of Organic Chemistry, University of Heidelberg , D-69120,
Heidelberg, Germany
Published online: 04 Oct 2006.
To cite this article: Hermann Irngartinger , Jochen Lichtenthäler , Rüdiger Herpich & Birgit
Stadler (1996) Solid State Behaviour of Vinyl Quinones, Molecular Crystals and Liquid Crystals
Science and Technology. Section A. Molecular Crystals and Liquid Crystals, 276:1-2, 349-360, DOI:
10.1080/10587259608039394
To link to this article: http://dx.doi.org/10.1080/10587259608039394
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or
howsoever caused arising directly or indirectly in connection with, in relation to or arising
out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden. Terms &
Conditions of access and use can be found at http://www.tandfonline.com/page/terms-
and-conditions