3-Methoxy-4-cyano-2,9-dioxabicyclo[4.3.0]non-3-e ne (1) was prepared by (4 + 2) cycloaddition reaction of methyl ${alpha}$-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 $alpha$ -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 $^{13}C$-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.