Photo-induced Cationic Ring-Opening Polymerization of 2-Alkenyl-4-methylene-1,3-dioxolanes by Benzylsulfonium Salt

Choi HK; Park J; Endo T

Korea Polymer Journal, Vol.2, No.1, 61-65, April, 1994

Preparation of 4-methylene-1,3-dioxolane derivative (Ia, Ib) with benzyl-4-hydroxy-phenyl methylsulfonium hexafluoro-antimonate (BSS_ is described. Unsaturated cyclic acetals Ia, Ib were synthesized by dehydrochlorinatio of 4-chloromethyl-1,3-dioxolane derivatives, which were easily prepared from acrolein derivative and 3-chloro-1,2-propane diol with sodium methoxide at ambient temperature. The photo-induced cationic polymerization with BSS yielded soluble poly-(keto-ether)s containing carbon-carbon double bond, wheres the cationic polymerization of Ia, Ib with CH₃SO₃H at ambient temperature produced crosslinked polymers.

[References]

Park J, Yokozawa T, Endo T, J. Polym. Sci. A: Polym. Chem., 31, 1141 (1993)
Takata T, Endo T, Yukigoseikagaku Kyokaishi, 48, 978 (1990)
Uno H, Endo T, J. Polym. Sci. C: Polym. Lett., 23, 359 (1985)
Uno H, Endo T, Chem. Lett., 1986 (1969)
Endo T, Sato H, Takata T, Macromolecules, 20, 1416 (1987)
Morio K, Murase H, Endo T, J. Appl. Polym. Sci., 32, 5727 (1986)
Kikkawa A, Takata T, Uno H, Hiza M, Endo T, J. Polym. Sci. C: Polym. Lett., 26, 73 (1989)
Lee SB, Takata T, Endo T, Chem. Lett., 1989 (1861)
Hamazu F, Akashi S, Koizumi T, Takata T, Endo T, J. Polym. Sci. A: Polym. Chem., 29, 1675 (1991)
Hamazu F, Akashi S, Koizumi T, Takata T, Endo T, Makromol. Chem. Rapid Commun., 13, 203 (1992)
Lin MP, Kim HB, Ikeda T, Endo T, J. Polym. Sci. A: Polym. Chem., 30, 2365 (1992)
Saeva FD, Breslin DT, Luss HR, J. Am. Chem. Soc., 113, 5333 (1991)

[1] Park J, Yokozawa T, Endo T, J. Polym. Sci. A: Polym. Chem., 31, 1141 (1993)

[2] Takata T, Endo T, Yukigoseikagaku Kyokaishi, 48, 978 (1990)

[3] Uno H, Endo T, J. Polym. Sci. C: Polym. Lett., 23, 359 (1985)

[4] Uno H, Endo T, Chem. Lett., 1986 (1969)

[5] Endo T, Sato H, Takata T, Macromolecules, 20, 1416 (1987)

[6] Morio K, Murase H, Endo T, J. Appl. Polym. Sci., 32, 5727 (1986)

[7] Kikkawa A, Takata T, Uno H, Hiza M, Endo T, J. Polym. Sci. C: Polym. Lett., 26, 73 (1989)

[8] Lee SB, Takata T, Endo T, Chem. Lett., 1989 (1861)

[9] Hamazu F, Akashi S, Koizumi T, Takata T, Endo T, J. Polym. Sci. A: Polym. Chem., 29, 1675 (1991)

[10] Hamazu F, Akashi S, Koizumi T, Takata T, Endo T, Makromol. Chem. Rapid Commun., 13, 203 (1992)

[11] Lin MP, Kim HB, Ikeda T, Endo T, J. Polym. Sci. A: Polym. Chem., 30, 2365 (1992)

[12] Saeva FD, Breslin DT, Luss HR, J. Am. Chem. Soc., 113, 5333 (1991)