Versatile carbon-carbon bond-forming polycondensation between terpene derivatives and malonic esters via palladium-catalyzed allylic substitution reaction

Macromolecules

Volumn 36, Issue 9, 2003, Pages 3007-3009

  Nomura, Nobuyoshi ^a   Yoshida, Nao ^a   Tsurugi, Ko ^a   Aoi, Keigo ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC SUBSTITUTION REACTIONS; CARBON-CARBON BOND FORMING; MALONIC ESTERS; TERPENE;

CHEMICAL BONDS; ESTERS; FUNCTIONAL POLYMERS; MONOMERS; PALLADIUM COMPOUNDS; POLYMERIZATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

POLYCONDENSATION;

EID: 0038103598     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma034125a     Document Type: Article

References (25)

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12. After our preliminary report, another type of palladium-catalyzed polymerization via π-allypalladium intermediates was reported: (a) Koizumi, T.; Sakamoto, J.; Gondo, Y.; Endo, T. Macromolecules 2000, 33, 7235.
13. (b) Koizumi, T.; Sakamoto, J.; Gondo, Y.; Endo, T. Macromolecules 2002, 35, 2898.
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18. Since reversible ionization of the Tsuji-Trost reaction has been reported, the cleavage of C-C bonds during polymerization could not be ruled out at thist stage: Amatore, C.; Gamez, S.; Jutand, A.; Meyer, G.; Moreno-Mañas, M.; Morral, L.; Pleixats, R. Chem.-Eur. J. 2000, 6, 3372.
19. Ten percent of the other following cosolvents were examined: THF, DMF, DMSO, and HMPA. These cosolvents might have participated in the catalysis somehow, not only as a polar cosolvent.
20. A review: Stridsberg, K. M.; Ryner, M .; Albertsson, A.-C. Adv. Polym. Sci. 2002, 157, 41.
21. 3N has been reported: (a) Andersson, P. G.; Schab, S. Organometallics 1995, 14, 1.
22. (b) Takacs, J. M.; Lawson, E. C.; Clement, F. J. Am. Chem. Soc. 1997, 119, 5956. The further mechanistic discussions about BSA and β-H-Pd elimination will be made with additional experiments in a future article.
23. n's got over 10 000; see ref 4c.
24. g's: poly [(1E, 5E)-8,8-bis(ethoxycarbonyl)-1,5-dimethylnona-1,5-dienylene] (entry 3), -16.5 °C; poly{oxy-[(2E,7E)-5,5-bis(ethoxycarbonyl)-3,7-dimethylnona-2,7-dienylene]} (entry 9), -3.2 °C; poly(p-toluenesulfonylimino-[(6E,11E)-9,9-bis(ethoxycarbonyl)-3,7,11,15-tetrame thylheptadeca-6,11-dienylene]) (entry 12), -23.0 °C; poly{oxy[(E)-2-ethoxycarbonyl-2,4,8-trimethyl-1-oxodec-4-enylene]} (12, entry 14), not detected.
25. An activated sludge was prepared so that the suspension concentration was 30 mg/L according to the Japan Industrial Standard JIS K 6950. The data were obtained by the average of three samples.