Abstract 2‐Butyl‐7‐methylene‐1,4,6‐trioxaspiro(4,4)nonane (7) 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 chargetransfer complex between 7 as an electron donor and AN as an electron acceptor.
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Pan et al. (1988) studied this question.
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