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Polymerization of cyclic monomers, 2 . Synthesis and radical polymerization of vinylcyclopropanes
Author(s) -
Zeuner Frank,
Moszner Norbert,
Rheinberger Volker
Publication year - 1996
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.1996.021970912
Subject(s) - polymer chemistry , polymerization , monomer , radical polymerization , living free radical polymerization , chemistry , reversible addition−fragmentation chain transfer polymerization , ionic polymerization , chain growth polymerization , organic chemistry , polymer
New 1,1‐disubstituted 2‐vinylcyclopropanes were synthesized by reaction of the corresponding malonyl diesters with trans ‐1,4‐dibromo‐2‐butene and of sodium hydride. The structure of the 2‐vinylcyclopropanes could be confirmed by elemental analysis, IR, 1 H NMR and 13 C NMR spectroscopy. Radical polymerization of the 2‐vinylcyclopropanes in bulk with 2,2′‐azoisobutyronitrile (AIBN) and di‐ tert ‐butyl peroxide (DtBPO), respectively, gives transparent polymers. In case of the liquid monomers, the polymerization is accompanied by negative volume changes. Spectroscopic investigations show that 2‐vinylcyclopropanes primarily undergo opening of the cyclopropane ring forming an 1,5‐addition polymer.