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References
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C. Dellichausen, MPI für Kohienforschung, Dissertation, Univ. Bochum (1968). In this thesis the author suggested the possibility of two isomers, methyl (Z,E)-3,7-cyclodecadienecarboxylate and methyl (E,Z)-3,7-cyclodecadienecarboxylate in the reaction of methyl acrylate and butadiene catalyzed by nickel ligand system. However, which of the two isomers was actually formed was not determined.
F. Quignard, M. Leconte, and J. M. Basset, Inorg. Chem., 26, 4272 (1987). Polymerization procedure by these catalyst systems was proceeded as follows; 10−5–10−4 mole of WCl4 (OAr)2 was placed in an ampoule in such a way that the catalyst concentration was 0.02 N. The solution was heated to 80°C and PbEt4 was syringed. The resulting catalyst mixture was allowed to stand for 20 min at 80°C. This solution was then transferred to an another ampoule with a cannula in which the monomer was kept at the reaction temperature. The ampoule was maintained at a given temperature for a given time period and the ampoule was opened. The reaction mixture was dropped into methanol wth rapid stirring, and the precipitate separated from the solution and washed twice with methanol. The final polymer was reprecipitated from chloroform into methanol. IR (film, cm−1) 1734.4 (ester carbonyl), 970.0 (–C=C–, trans), 717.4 (–C=C–, cis); 1H NMR (CDCl3, ppm) 1.2—2.7 (br, m; 11H), 3.5—3.7 (s; 3H), 5.2—5.6 (br, m; 4H); 13C NMR (CDCl3, ppm) 28.6 (–CH2–), 31.3, 31.7 (cis allylic carbons), 32.8, 33.0 (trans allylic carbons), 46.4 (–ˈCH-CO2–), 52.5 (–OCH3), 127.8–132.6 (–C=C–, cis and trans), 177.2 (–CO2–).
L. Hocks, A. J. Hubert, and Ph. Teyssié, Tetrahedron Lett., 29, 2719 (1973).
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Cho, I., Bae, S. Ring-Opening Polymerization of Methyl (Z,E or E, Z)-3,7-Cyclodecadienecarboxylate by Metathesis Catalysts. Polym J 23, 1283–1286 (1991). https://doi.org/10.1295/polymj.23.1283
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DOI: https://doi.org/10.1295/polymj.23.1283