SYNTHESIS AND POLYMERIZATION OF 2-BUTYL-7-METHYLENE-1,4,6-TRIOXASPIRO(4,4)NONANE

2-Butyl-7-methylene-1,4,6-trioxaspiro(4,4)nonane was prepared by the reaction of 2-(bromomethyl)-5-oxo-tetrahydrofuran with 1, 2-epoxyhexane, followed by dehydrobromination. Compound 7 could be polymerized by free radical initiators to give a viscous polymer. The IR and NMR spectra of the polymers indicated that the polymer structure contained ester and ketone units in the backbone, and a cyclic acetal side chain. Compound 7 readily copolymerized with acrylonitrile in the presence and absence of radical initiators, but did not copolymerize well with styrene. Ultraviolet spectra suggest that the spontaneous polymerization proceeds via a charge transfer complex between 7 as an electron donor and AN as an electron acceptor.