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Synfacts 2006(12): 1231-1231  
DOI: 10.1055/s-2006-955585
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Insertion Polymerization of Cyclobutenes by Detouring Pericyclic Opening

Contributor(s): Timothy M. Swager, Changsik Song
K. Seto, B. M. Novak*
North Carolina State University, Raleigh, USA
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

In this communication, Seto and Novak cleverly designed insertion-polymerizable cyclobutenes. These molecules generally are difficult to polymerize in an insertion fashion since they isomerize to butadienes through pericyclic ring-opening reactions. By locking the cyclobutene with a cis-fused ring system, they were able to achieve fairly high-molecular-weight polymers (Mn is up to 155,000) after optimizing conditions.