SYNTHESIS AND RADICAL RING-OPENING POLYMERIZATION OF VINYLCYCLOPROPANES REARING VINYLSILANE GROUPS

Synthesis and radical polymerization of novel vinylcyclopropanes; 1-ca rboethoxy-2-trimethylsilyl-2-vinylcyclopropane (1a) and carboethoxy-2- (1-trimethylsilyl)-vinylcyclopropane (1b), were examined. la and 1b we re prepared by the coupling reaction of 2-trimethylsilylbutadiene with ethyl diazoacetate, which was prepared from glycine ethyl ester hydro chloride. The radical polymerization of 1a and 1b was carried out at 6 0 degrees C in bulk for 40 h in the presence of 2,2'-azobis(isobutyron itrile) (5 mol % vs. monomer). Poly(1) consisted of a 1,5-ring-opened unit. Desilylation reaction of poly(1) proceeded quantitatively in aqu eous hydrochloric acid. (C) 1998 John Wiley & Sons, Inc.