Ring-opening polymerization of cyclobutane adduct of dimethyl 1,1-dicyanoethylene-2,2-dicarboxylate and ethyl vinyl ether

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 35, Issue 8, 1997, Pages 1563-1570

  Yokozawa, Tsutomu ^a   Wakabayashi, Yuki ^a   Kimura, Takamasa ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

Alternating copolymer; Cyclobutane; Dimethyl 1,1 dicyanoethylene 2,2 dicarboxylate; Ring opening polymerization; Vinyl ether

Indexed keywords

ACETIC ACID; AMINES; AMMONIUM COMPOUNDS; CATALYSTS; HALOGEN COMPOUNDS; INITIATORS (CHEMICAL); METHANOL; POLYETHERS; REACTION KINETICS; RING OPENING POLYMERIZATION;

CHAIN TRANSFER REACTIONS; CYCLOBUTANE ADDUCTS; LEWIS ACIDS;

COPOLYMERS;

EID: 0031162325     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0518(199706)35:8<1563::AID-POLA25>3.0.CO;2-4     Document Type: Article

References (28)

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17. For other cycloadditions of DDED, see: (a) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 108, 4920 (1986); (b) R. Sustmann, K. Luecking, G. Kopp, and M. Rese, Angew. Chem., 101, 1701 (1989); (c) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 113, 1308 (1991); (d) A. B. Padias, T. P. Tien, and H. K. Hall, Jr., J. Org. Chem., 56, 5540 (1991); (e) R. Sustmann and I. Siangouri-Feulner, Chem. Ber., 126, 1241 (1993); (f) W. Srisiri, A. B. Padias, and H. K. Hall, Jr., J. Org. Chem., 59, 5424 (1994); (g) K. Luecking, M. Rese, and R. Sustmann, Liebigs Ann., 1129 (1995); (h) M. Rese, M. Dern, K. Luecking, and R. Sustmann, Liebigs Ann., 1139 (1995).
18. For other cycloadditions of DDED, see: (a) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 108, 4920 (1986); (b) R. Sustmann, K. Luecking, G. Kopp, and M. Rese, Angew. Chem., 101, 1701 (1989); (c) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 113, 1308 (1991); (d) A. B. Padias, T. P. Tien, and H. K. Hall, Jr., J. Org. Chem., 56, 5540 (1991); (e) R. Sustmann and I. Siangouri-Feulner, Chem. Ber., 126, 1241 (1993); (f) W. Srisiri, A. B. Padias, and H. K. Hall, Jr., J. Org. Chem., 59, 5424 (1994); (g) K. Luecking, M. Rese, and R. Sustmann, Liebigs Ann., 1129 (1995); (h) M. Rese, M. Dern, K. Luecking, and R. Sustmann, Liebigs Ann., 1139 (1995).
19. For other cycloadditions of DDED, see: (a) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 108, 4920 (1986); (b) R. Sustmann, K. Luecking, G. Kopp, and M. Rese, Angew. Chem., 101, 1701 (1989); (c) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 113, 1308 (1991); (d) A. B. Padias, T. P. Tien, and H. K. Hall, Jr., J. Org. Chem., 56, 5540 (1991); (e) R. Sustmann and I. Siangouri-Feulner, Chem. Ber., 126, 1241 (1993); (f) W. Srisiri, A. B. Padias, and H. K. Hall, Jr., J. Org. Chem., 59, 5424 (1994); (g) K. Luecking, M. Rese, and R. Sustmann, Liebigs Ann., 1129 (1995); (h) M. Rese, M. Dern, K. Luecking, and R. Sustmann, Liebigs Ann., 1139 (1995).
20. For other cycloadditions of DDED, see: (a) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 108, 4920 (1986); (b) R. Sustmann, K. Luecking, G. Kopp, and M. Rese, Angew. Chem., 101, 1701 (1989); (c) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 113, 1308 (1991); (d) A. B. Padias, T. P. Tien, and H. K. Hall, Jr., J. Org. Chem., 56, 5540 (1991); (e) R. Sustmann and I. Siangouri-Feulner, Chem. Ber., 126, 1241 (1993); (f) W. Srisiri, A. B. Padias, and H. K. Hall, Jr., J. Org. Chem., 59, 5424 (1994); (g) K. Luecking, M. Rese, and R. Sustmann, Liebigs Ann., 1129 (1995); (h) M. Rese, M. Dern, K. Luecking, and R. Sustmann, Liebigs Ann., 1139 (1995).
21. For other cycloadditions of DDED, see: (a) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 108, 4920 (1986); (b) R. Sustmann, K. Luecking, G. Kopp, and M. Rese, Angew. Chem., 101, 1701 (1989); (c) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 113, 1308 (1991); (d) A. B. Padias, T. P. Tien, and H. K. Hall, Jr., J. Org. Chem., 56, 5540 (1991); (e) R. Sustmann and I. Siangouri-Feulner, Chem. Ber., 126, 1241 (1993); (f) W. Srisiri, A. B. Padias, and H. K. Hall, Jr., J. Org. Chem., 59, 5424 (1994); (g) K. Luecking, M. Rese, and R. Sustmann, Liebigs Ann., 1129 (1995); (h) M. Rese, M. Dern, K. Luecking, and R. Sustmann, Liebigs Ann., 1139 (1995).
22. For other cycloadditions of DDED, see: (a) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 108, 4920 (1986); (b) R. Sustmann, K. Luecking, G. Kopp, and M. Rese, Angew. Chem., 101, 1701 (1989); (c) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 113, 1308 (1991); (d) A. B. Padias, T. P. Tien, and H. K. Hall, Jr., J. Org. Chem., 56, 5540 (1991); (e) R. Sustmann and I. Siangouri-Feulner, Chem. Ber., 126, 1241 (1993); (f) W. Srisiri, A. B. Padias, and H. K. Hall, Jr., J. Org. Chem., 59, 5424 (1994); (g) K. Luecking, M. Rese, and R. Sustmann, Liebigs Ann., 1129 (1995); (h) M. Rese, M. Dern, K. Luecking, and R. Sustmann, Liebigs Ann., 1139 (1995).
23. For other cycloadditions of DDED, see: (a) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 108, 4920 (1986); (b) R. Sustmann, K. Luecking, G. Kopp, and M. Rese, Angew. Chem., 101, 1701 (1989); (c) T. Gotoh, A. B. Padias, and H. K. Hall, Jr., J. Am. Chem. Soc., 113, 1308 (1991); (d) A. B. Padias, T. P. Tien, and H. K. Hall, Jr., J. Org. Chem., 56, 5540 (1991); (e) R. Sustmann and I. Siangouri-Feulner, Chem. Ber., 126, 1241 (1993); (f) W. Srisiri, A. B. Padias, and H. K. Hall, Jr., J. Org. Chem., 59, 5424 (1994); (g) K. Luecking, M. Rese, and R. Sustmann, Liebigs Ann., 1129 (1995); (h) M. Rese, M. Dern, K. Luecking, and R. Sustmann, Liebigs Ann., 1139 (1995).
24. Although the 1 : 1 copolymer of DDED with VE was not investigated in detail in the reference 9, the structure of the copolymer of DDED with styrene was studied in great detail. On this basis, the copolymer of DDED with VE obtained by the radical copolymerization would have the same structure of the polymer by the ring-opening polymerization of 3. This is due to the fact that the structure of the cyclobutane is governed by the maximal stabilization of zwitterionic intermediate, while the structure of the copolymer is governed mostly by steric hindrance. (Equation Presented)
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