ISSN:
0025-116X
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The cyclic ketene acetal, 2-methylene-4-phenyl-1,3-dioxolane (3), was shown to undergo free radical ring-opening polymerization to produce the polyester, poly[γ-(β-phenyl)butyrolactone]. The monomer 3 was synthesized by an acetal exchange reaction of chloroacetaldehyde dimethyl acetal with styrene glycol in an 87% yield followed by dehydrochlorination of the resulting cis and trans-2-chloromethyl-4-phenyl-1,3-dioxolane (2) with potassium tert-butoxide in tert-butyl alcohol in a 70% yield. 3 was shown to undergo essentially quantitative free radical ring-opening at all temperatures from 60-150°C and also nearly complete regioselective ring-opening with cleavage to give the more highly stable secondary benzyl free radical. Even in free radical copolymerization with styrene, methyl methacrylate, vinyl acetate, or 4-vinylpyridine, 3 gives essentially complete ring opening to introduce an ester groups into the backbone of the addition copolymer. The structures of the polymers were established by elemental analysis and 1H and 13C NMR spectroscopy.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/macp.1982.021830811
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