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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 16, Number 8
BKCSDE 16(8)
August 20, 1995 

Polymerization of 4-Methylene-1,3-dioxolane Derivatives
Seung-Jae Lee, Jeong-Ki Park, Myoung-Seon Gong*
The 4-methylene-1,3-dioxolane derivatives, 2-[(2-methoxyethoxy)methyl]-4-methylene-1,3-diox olane (4a), 4-methylene-2-phenyl-1,3-dioxolane (4b), 4-methylene-2-(p-methoxyphenyl)-1,3-dioxolane (4c), 4-methylene-2-[p-(2-methoxyethoxy)phenyl]-1,3-di oxolane (4d) were prepared by acetalization, followed by dehydrochlorination with potassium tert-butoxide (t-BuOK). They were readily polymerized with boron trifluoride and tungsten hexachloride. Monomer 4a underwent 70% ring-opening polymerization with WCl6, whereas monomers 4b and 4c polymerized with quantitative ring-opening to form poly(keto ether)s. Especially 4d underwent Claisen-type isomerization to afford 2-[4-(2-methoxyethoxy)phenyl]-3(2H)-dihydrofuran one in the presence of WCl6. Acid catalyzed mechanisms were suggested for the behaviors of polymerization and isomerization of 4-methylene-1,3-dioxolane derivatives with BF3 and WCl6 catalyst.
769 - 773
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