Coupling polymerization of monofunctional allene derivatives with malonates bearing aryl halides moieties via π-allylpalladium complex

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 35, Issue 10, 1997, Pages 2097-2103

  Miyaki, Nobuyuki ^a   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Allene derivatives; Multibranched polymer; Nucleophile bearing aryl halides moieties; Palladium catalyst

Indexed keywords

CATALYSTS; CHEMICAL BONDS; CHEMICAL REACTIONS; DERIVATIVES; INFRARED SPECTROSCOPY;

ALLENE DERIVATIVES; COUPLING REACTION; MULTIBRANCHED POLYMER; NUCLEOPHILE BEARING ARYL HALIDES MOIETIES;

POLYMERIZATION;

EID: 0031188126     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0518(19970730)35:10<2097::AID-POLA24>3.0.CO;2-A     Document Type: Article

References (23)

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14. n = 2000) were obtained probably due to the insufficient formation of nucleophilic moieties (i.e., the carbanion) or any side reactions such as transesterification. Thus, sodium hydride was used as a base for the series of this study.
15. d10), respectively, were observed at 9.5°C and 316.8, respectively.
16. The content of the reduced end (i.e., phenoxy moieties) was rather higher in the present polymerization in comparison with the previous system using bisallene, aryl dihalide, and sodium diethyl malonate (see ref. 4). The difference might be arisen from the side reaction of the palladium catalyst with sodium hydride to produce a palladium hydride, which brought about the reduced end. In fact, when palladium acetate and sodium hydride were mixed in 1,4-dioxane, the deposition of palladium metal and the evolution of hydrogen were observed. For the palladium hydride formation, see: (a) E. J. Corey and S. W. Wright, J. Org. Chem., 55, 1670 (1990); (b) F. Guibe, P. Four, and H. Riviere, Chem. Comm., 432 (1980); (c) J. Tsuji and I. Shimizu, J. Synth. Org. Chem. Jpn., 48, 1016 (1990); (d) E. Keinan and N. Greenspoon, Tetrahedron Lett., 23, 241 (1982); (e) H. Kotake, T. Yamamoto, and H. Kinoshita, Chem. Lett., 1331 (1982); (f) R. O. Hutchins and K. Learn, J. Org. Chem., 47, 4380 (1982); (g) H. Matsushita and E. Negishi, J. Org. Chem., 47, 4161 (1982).
17. The content of the reduced end (i.e., phenoxy moieties) was rather higher in the present polymerization in comparison with the previous system using bisallene, aryl dihalide, and sodium diethyl malonate (see ref. 4). The difference might be arisen from the side reaction of the palladium catalyst with sodium hydride to produce a palladium hydride, which brought about the reduced end. In fact, when palladium acetate and sodium hydride were mixed in 1,4-dioxane, the deposition of palladium metal and the evolution of hydrogen were observed. For the palladium hydride formation, see: (a) E. J. Corey and S. W. Wright, J. Org. Chem., 55, 1670 (1990); (b) F. Guibe, P. Four, and H. Riviere, Chem. Comm., 432 (1980); (c) J. Tsuji and I. Shimizu, J. Synth. Org. Chem. Jpn., 48, 1016 (1990); (d) E. Keinan and N. Greenspoon, Tetrahedron Lett., 23, 241 (1982); (e) H. Kotake, T. Yamamoto, and H. Kinoshita, Chem. Lett., 1331 (1982); (f) R. O. Hutchins and K. Learn, J. Org. Chem., 47, 4380 (1982); (g) H. Matsushita and E. Negishi, J. Org. Chem., 47, 4161 (1982).
18. The content of the reduced end (i.e., phenoxy moieties) was rather higher in the present polymerization in comparison with the previous system using bisallene, aryl dihalide, and sodium diethyl malonate (see ref. 4). The difference might be arisen from the side reaction of the palladium catalyst with sodium hydride to produce a palladium hydride, which brought about the reduced end. In fact, when palladium acetate and sodium hydride were mixed in 1,4-dioxane, the deposition of palladium metal and the evolution of hydrogen were observed. For the palladium hydride formation, see: (a) E. J. Corey and S. W. Wright, J. Org. Chem., 55, 1670 (1990); (b) F. Guibe, P. Four, and H. Riviere, Chem. Comm., 432 (1980); (c) J. Tsuji and I. Shimizu, J. Synth. Org. Chem. Jpn., 48, 1016 (1990); (d) E. Keinan and N. Greenspoon, Tetrahedron Lett., 23, 241 (1982); (e) H. Kotake, T. Yamamoto, and H. Kinoshita, Chem. Lett., 1331 (1982); (f) R. O. Hutchins and K. Learn, J. Org. Chem., 47, 4380 (1982); (g) H. Matsushita and E. Negishi, J. Org. Chem., 47, 4161 (1982).
19. The content of the reduced end (i.e., phenoxy moieties) was rather higher in the present polymerization in comparison with the previous system using bisallene, aryl dihalide, and sodium diethyl malonate (see ref. 4). The difference might be arisen from the side reaction of the palladium catalyst with sodium hydride to produce a palladium hydride, which brought about the reduced end. In fact, when palladium acetate and sodium hydride were mixed in 1,4-dioxane, the deposition of palladium metal and the evolution of hydrogen were observed. For the palladium hydride formation, see: (a) E. J. Corey and S. W. Wright, J. Org. Chem., 55, 1670 (1990); (b) F. Guibe, P. Four, and H. Riviere, Chem. Comm., 432 (1980); (c) J. Tsuji and I. Shimizu, J. Synth. Org. Chem. Jpn., 48, 1016 (1990); (d) E. Keinan and N. Greenspoon, Tetrahedron Lett., 23, 241 (1982); (e) H. Kotake, T. Yamamoto, and H. Kinoshita, Chem. Lett., 1331 (1982); (f) R. O. Hutchins and K. Learn, J. Org. Chem., 47, 4380 (1982); (g) H. Matsushita and E. Negishi, J. Org. Chem., 47, 4161 (1982).
20. The content of the reduced end (i.e., phenoxy moieties) was rather higher in the present polymerization in comparison with the previous system using bisallene, aryl dihalide, and sodium diethyl malonate (see ref. 4). The difference might be arisen from the side reaction of the palladium catalyst with sodium hydride to produce a palladium hydride, which brought about the reduced end. In fact, when palladium acetate and sodium hydride were mixed in 1,4-dioxane, the deposition of palladium metal and the evolution of hydrogen were observed. For the palladium hydride formation, see: (a) E. J. Corey and S. W. Wright, J. Org. Chem., 55, 1670 (1990); (b) F. Guibe, P. Four, and H. Riviere, Chem. Comm., 432 (1980); (c) J. Tsuji and I. Shimizu, J. Synth. Org. Chem. Jpn., 48, 1016 (1990); (d) E. Keinan and N. Greenspoon, Tetrahedron Lett., 23, 241 (1982); (e) H. Kotake, T. Yamamoto, and H. Kinoshita, Chem. Lett., 1331 (1982); (f) R. O. Hutchins and K. Learn, J. Org. Chem., 47, 4380 (1982); (g) H. Matsushita and E. Negishi, J. Org. Chem., 47, 4161 (1982).
21. The content of the reduced end (i.e., phenoxy moieties) was rather higher in the present polymerization in comparison with the previous system using bisallene, aryl dihalide, and sodium diethyl malonate (see ref. 4). The difference might be arisen from the side reaction of the palladium catalyst with sodium hydride to produce a palladium hydride, which brought about the reduced end. In fact, when palladium acetate and sodium hydride were mixed in 1,4-dioxane, the deposition of palladium metal and the evolution of hydrogen were observed. For the palladium hydride formation, see: (a) E. J. Corey and S. W. Wright, J. Org. Chem., 55, 1670 (1990); (b) F. Guibe, P. Four, and H. Riviere, Chem. Comm., 432 (1980); (c) J. Tsuji and I. Shimizu, J. Synth. Org. Chem. Jpn., 48, 1016 (1990); (d) E. Keinan and N. Greenspoon, Tetrahedron Lett., 23, 241 (1982); (e) H. Kotake, T. Yamamoto, and H. Kinoshita, Chem. Lett., 1331 (1982); (f) R. O. Hutchins and K. Learn, J. Org. Chem., 47, 4380 (1982); (g) H. Matsushita and E. Negishi, J. Org. Chem., 47, 4161 (1982).
22. The content of the reduced end (i.e., phenoxy moieties) was rather higher in the present polymerization in comparison with the previous system using bisallene, aryl dihalide, and sodium diethyl malonate (see ref. 4). The difference might be arisen from the side reaction of the palladium catalyst with sodium hydride to produce a palladium hydride, which brought about the reduced end. In fact, when palladium acetate and sodium hydride were mixed in 1,4-dioxane, the deposition of palladium metal and the evolution of hydrogen were observed. For the palladium hydride formation, see: (a) E. J. Corey and S. W. Wright, J. Org. Chem., 55, 1670 (1990); (b) F. Guibe, P. Four, and H. Riviere, Chem. Comm., 432 (1980); (c) J. Tsuji and I. Shimizu, J. Synth. Org. Chem. Jpn., 48, 1016 (1990); (d) E. Keinan and N. Greenspoon, Tetrahedron Lett., 23, 241 (1982); (e) H. Kotake, T. Yamamoto, and H. Kinoshita, Chem. Lett., 1331 (1982); (f) R. O. Hutchins and K. Learn, J. Org. Chem., 47, 4380 (1982); (g) H. Matsushita and E. Negishi, J. Org. Chem., 47, 4161 (1982).
23. Side reactions such as the reduction (see ref. 7) and the transesterification may not become negligible at higher reaction temperature.