Free radical carbonylation of 1,4-cis-polybutadiene

Journal of the American Chemical Society

Volumn 118, Issue 30, 1996, Pages 7223-7224

  Chatgilialoglu, C ^a   Ferreri, C ^a,b   Sommazzi, A ^c  

^a CNR   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c Istituto Guido Donegani SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

POLYENE;

ARTICLE; DRUG STRUCTURE; INFRARED SPECTROPHOTOMETRY; POLYMERIZATION;

EID: 0029745536     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9543053     Document Type: Article

References (24)

1. For reviews, see: (a) Sen, A. Adv. Polym. Sci. 1986, 73/74, 125. (b) Sen, A. Acc. Chem. Res. 1993, 26, 303.
2. For reviews, see: (a) Sen, A. Adv. Polym. Sci. 1986, 73/74, 125. (b) Sen, A. Acc. Chem. Res. 1993, 26, 303.
3. For the initial work, see: Brubaker, M. M. Coffman, D. D.; Hoehn, H. H. J. Am. Chem. Soc: 1952, 74, 1509.
4. For recent work, see: (a) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (b) Jiang, Z.; Boyer, M. T.; Sen, A. J. Am. Chem. Soc. 1995, 117, 7037. (c) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (d) Forbes, M. D. E.; Ruberu, S. R.; Nachtigalliva, D.; Jordan, K. D.; Barborak, J. C. J. Am. Chem. Soc: 1995, 117, 3946.
5. For recent work, see: (a) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (b) Jiang, Z.; Boyer, M. T.; Sen, A. J. Am. Chem. Soc. 1995, 117, 7037. (c) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (d) Forbes, M. D. E.; Ruberu, S. R.; Nachtigalliva, D.; Jordan, K. D.; Barborak, J. C. J. Am. Chem. Soc: 1995, 117, 3946.
6. For recent work, see: (a) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (b) Jiang, Z.; Boyer, M. T.; Sen, A. J. Am. Chem. Soc. 1995, 117, 7037. (c) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (d) Forbes, M. D. E.; Ruberu, S. R.; Nachtigalliva, D.; Jordan, K. D.; Barborak, J. C. J. Am. Chem. Soc: 1995, 117, 3946.
7. For recent work, see: (a) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130. (b) Jiang, Z.; Boyer, M. T.; Sen, A. J. Am. Chem. Soc. 1995, 117, 7037. (c) Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455. (d) Forbes, M. D. E.; Ruberu, S. R.; Nachtigalliva, D.; Jordan, K. D.; Barborak, J. C. J. Am. Chem. Soc: 1995, 117, 3946.
8. Polyketones with a low carbon monoxide content are currently used as photodegradable plastics. For example, see: (a) Bremer, W. P. Polym. Plast. Technol. Eng. 1982, 18, 137. (b) Leaversuch, R. Mod. Plast. Int. 1987, 17, 64.
9. Polyketones with a low carbon monoxide content are currently used as photodegradable plastics. For example, see: (a) Bremer, W. P. Polym. Plast. Technol. Eng. 1982, 18, 137. (b) Leaversuch, R. Mod. Plast. Int. 1987, 17, 64.
10. Drent, E.; Budzelaar, P. H. M. Chem. Rev. 1996, 96, 663.
11. Sommazzi, A.; Cardi, N.; Garbassi, F.; Chatgilialoglu, C. U.S. Patent 5,369,187, 1994.
12. The polybutadiene which has been used in this work contains 1,4-cis units of more than 98% and an average viscosimetric molecular weight of 200 000 as measured in toluene at 30 °C.
13. 2 content was determined by measuring the thermal conductivity of gases deriving from the pyrolysis of the sample. Therefore, the CO content is an indirect measurement of the amount of structural cycloketonic units.
14. 1H NMR spectra also showed some important structural features, in particular at higher CO incorporation. The NMR spectra of polymer B are available in the supporting information.
15. m ≃ 300 °C. It is evident that for the polymer with the higher incorporation of CO (20%), the thermal properties of the material change substantially. The thermograms are available in the supporting information.
16. (a) Ryu, I; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177 and references cited therein.
17. (b) Ryu, I.; Kusano, K.; Hasegawa, M.; Kambe. N.; Sonoda, N. J. Chem. Soc., Chem Commun. 1991, 1018.
18. (a) Dowd, P.; Zhang, W, Chem. Rev. 1993, 93, 2091.
19. (b) Brown, C. E.; Neville, A. G.; Rayner, D. M.; Ingold, K. U.; Lusztyk, J. Aust. J. Chem. 1995, 48, 363 and references cited therein.
20. The diastereoisomerism is expected to be lost in the formation of the corresponding carbon-centered radical.
21. In comparison with the retention time of their authentic samples.
22. Chatgilialoglu, C.; Dickhaut, J.; Giese, B. J. Org. Chem. 1991, 56, 6399.
23. Newcomb, M. Tetrahedron 1993, 49, 1151.
24. Chatgilialoglu, C.; Ferreri, C.; Lucarini, M.; Pedrielli, P.; Pedulli, G. F. Organometallics 1995, 14, 2672.