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Synthesis and polymerization of vinylcyclopropanes

✍ Scribed by Norbert Moszner; Frank Zeuner; Thomas Völkel; Volker Rheinberger

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
222 KB
Volume
200
Category
Article
ISSN
1022-1352

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✦ Synopsis

Vinylcyclopropanes are important synthetic intermediates in organic chemistry and are mostly synthesized by the simultaneous introduction of the cyclopropane and the vinyl unit, e. g., by the reaction of trans-1,4-dihalobutenes with b-dicarbonyl compounds or the addition of carbenes to dienes. The polymerization of vinylcyclopropane itself results in vinyl polymers with predominantly 1,2-structural units. The radical polymerization of substituted vinylcyclopropanes results in polymers with mainly 1,5-ring-opened units, whereby radical stabilizing substituents or electron-withdrawing groups increase the radical polymerizability and the ring-opening ability. The vinylcyclopropanes undergo a radical copolymerization with other vinyl monomers, such as methacrylates, and, in comparison to the polymerization of these linear vinyl monomers, the vinylcyclopropanes show a significantly lower volume shrinkage during ring-opening polymerization. Hybrid vinylcyclopropanes are polymerized step-by-step under formation of reactive polymers or polymer networks. Multifunctional cross-linking vinylcyclopropanes can be used as new low-shrinking matrix monomers for photopolymerizable materials. In addition, the sol-gel process of trialkoxysilyl-functionalized vinylcyclopropanes affords low shrinking organic-inorganic nanocomposites.

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Polymerization of cyclic monomers, 2. Sy
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