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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 9, Number 3
March 20, 1988 

Synthesis of Alternating Head-to-Head Copolymer of Methyl α-cyanoacrylate and 2,3-Dihydrofuran. Ring-Opening Polymerization of 3-Methoxy-4-cyano-2,9-dioxabicyclo[4.3.0]non-3-ene
Ju-Yeon Lee*, Iwhan Cho
3-Methoxy-4-cyano-2,9-dioxabicyclo[4.3.0]non-3-e ne (1) was prepared by (4 + 2) cycloaddition reaction of methyl α-cyanoacrylate with 2,3-dihydrofuran. Compound 1 was ring-open polymerized by cationic catalyst such as boron trifluoride etherate to obtain alternating head-to-head (H-H) copolymer (2) of methyl α -cyanoacrylate and 2,3-dihydrofuran. For comparison, head-to-tail (H-T) copolymer (3) was also prepared by free radical copolymerization of the corresponding monomers. The H-H copolymer exhibited minor differences in its 1H-NMR and IR spectra, but in the 13C-NMR spectra significant differences were observed between the H-H and H-T copolymers. All of the H-H and H-T copolymers were soluble in common solvents and the inherent viscosities were in the range 0.2-0.3 dl/g.
176 - 179
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