Metathesis polymerization of phenylacetylene by arene metal tricarbonyl complexes promoted by chloranil acceptor

Organometallics

Volumn 16, Issue 22, 1997, Pages 4940-4942

  Vijayaraj, Thorappadi Anantharaj ^a   Sundararajan, Govindarajan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001672714     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970192f     Document Type: Article

References (54)

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6. For some key references to CO insertion chemistry in 17/19-electron complexes, see: (a) Therien, M. J.; Trogler, W. C. J. Am. Chem. Soc. 1987, 109, 5127. (b) Donovan, B. T.; Geiger, W. P. Organometallics 1990, 9, 865. (c) Tracy, A. A.; Eriks, K.; Prock, A.; Giering, W. E. Organometallics 1990, 9, 1399. (d) Giering, W. E. Acc. Chem. Res. 1995, 28, 351.
7. For some key references to CO insertion chemistry in 17/19-electron complexes, see: (a) Therien, M. J.; Trogler, W. C. J. Am. Chem. Soc. 1987, 109, 5127. (b) Donovan, B. T.; Geiger, W. P. Organometallics 1990, 9, 865. (c) Tracy, A. A.; Eriks, K.; Prock, A.; Giering, W. E. Organometallics 1990, 9, 1399. (d) Giering, W. E. Acc. Chem. Res. 1995, 28, 351.
8. For some key references to CO insertion chemistry in 17/19-electron complexes, see: (a) Therien, M. J.; Trogler, W. C. J. Am. Chem. Soc. 1987, 109, 5127. (b) Donovan, B. T.; Geiger, W. P. Organometallics 1990, 9, 865. (c) Tracy, A. A.; Eriks, K.; Prock, A.; Giering, W. E. Organometallics 1990, 9, 1399. (d) Giering, W. E. Acc. Chem. Res. 1995, 28, 351.
9. For some key references to CO insertion chemistry in 17/19-electron complexes, see: (a) Therien, M. J.; Trogler, W. C. J. Am. Chem. Soc. 1987, 109, 5127. (b) Donovan, B. T.; Geiger, W. P. Organometallics 1990, 9, 865. (c) Tracy, A. A.; Eriks, K.; Prock, A.; Giering, W. E. Organometallics 1990, 9, 1399. (d) Giering, W. E. Acc. Chem. Res. 1995, 28, 351.
10. For ligand substitutions, see: (a) Hershberger, J. W.; Klingler, R. J.; Kochi, J. K. J. Am. Chem. Soc. 1983, 105, 61. (b) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (c) Poli, R.; Owens, B. E.; Linck, R. G. J. Am. Chem. Soc. 1992, 114, 1302. (d) Huang, Y.; Carpenter, G. B.; Sweigart, D. A.; Chang, Y. K.; Lee, B.Y. Organometallics 1995, 14, 1423. (e) Huang, Y.; Neto, C. C.; Pevear, K. A.; Banaszak Holl, M. M.; Sweigart, D. A.; Chang, Y. K. Inorg. Chim. Acta 1994, 226, 53.
11. For ligand substitutions, see: (a) Hershberger, J. W.; Klingler, R. J.; Kochi, J. K. J. Am. Chem. Soc. 1983, 105, 61. (b) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (c) Poli, R.; Owens, B. E.; Linck, R. G. J. Am. Chem. Soc. 1992, 114, 1302. (d) Huang, Y.; Carpenter, G. B.; Sweigart, D. A.; Chang, Y. K.; Lee, B.Y. Organometallics 1995, 14, 1423. (e) Huang, Y.; Neto, C. C.; Pevear, K. A.; Banaszak Holl, M. M.; Sweigart, D. A.; Chang, Y. K. Inorg. Chim. Acta 1994, 226, 53.
12. For ligand substitutions, see: (a) Hershberger, J. W.; Klingler, R. J.; Kochi, J. K. J. Am. Chem. Soc. 1983, 105, 61. (b) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (c) Poli, R.; Owens, B. E.; Linck, R. G. J. Am. Chem. Soc. 1992, 114, 1302. (d) Huang, Y.; Carpenter, G. B.; Sweigart, D. A.; Chang, Y. K.; Lee, B.Y. Organometallics 1995, 14, 1423. (e) Huang, Y.; Neto, C. C.; Pevear, K. A.; Banaszak Holl, M. M.; Sweigart, D. A.; Chang, Y. K. Inorg. Chim. Acta 1994, 226, 53.
13. For ligand substitutions, see: (a) Hershberger, J. W.; Klingler, R. J.; Kochi, J. K. J. Am. Chem. Soc. 1983, 105, 61. (b) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (c) Poli, R.; Owens, B. E.; Linck, R. G. J. Am. Chem. Soc. 1992, 114, 1302. (d) Huang, Y.; Carpenter, G. B.; Sweigart, D. A.; Chang, Y. K.; Lee, B.Y. Organometallics 1995, 14, 1423. (e) Huang, Y.; Neto, C. C.; Pevear, K. A.; Banaszak Holl, M. M.; Sweigart, D. A.; Chang, Y. K. Inorg. Chim. Acta 1994, 226, 53.
14. For ligand substitutions, see: (a) Hershberger, J. W.; Klingler, R. J.; Kochi, J. K. J. Am. Chem. Soc. 1983, 105, 61. (b) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (c) Poli, R.; Owens, B. E.; Linck, R. G. J. Am. Chem. Soc. 1992, 114, 1302. (d) Huang, Y.; Carpenter, G. B.; Sweigart, D. A.; Chang, Y. K.; Lee, B.Y. Organometallics 1995, 14, 1423. (e) Huang, Y.; Neto, C. C.; Pevear, K. A.; Banaszak Holl, M. M.; Sweigart, D. A.; Chang, Y. K. Inorg. Chim. Acta 1994, 226, 53.
15. For ETC-catalyzed polymerizations, see: (a) Desbois, M. H.; Astruc, D. J. Chem. Soc., Chem. Commun. 1988, 472. (b) Desbois, M. H.; Astruc, D. New J. Chem. 1989, 39, 595. (c) Ganesamoorthy, S.; Sundararajan, G. Macromolecules 1992, 25, 2060. (d) Ganesamoorthy, S.; Sundararajan, G. J. Mol. Catal. 1992, 76, 335.
16. For ETC-catalyzed polymerizations, see: (a) Desbois, M. H.; Astruc, D. J. Chem. Soc., Chem. Commun. 1988, 472. (b) Desbois, M. H.; Astruc, D. New J. Chem. 1989, 39, 595. (c) Ganesamoorthy, S.; Sundararajan, G. Macromolecules 1992, 25, 2060. (d) Ganesamoorthy, S.; Sundararajan, G. J. Mol. Catal. 1992, 76, 335.
17. For ETC-catalyzed polymerizations, see: (a) Desbois, M. H.; Astruc, D. J. Chem. Soc., Chem. Commun. 1988, 472. (b) Desbois, M. H.; Astruc, D. New J. Chem. 1989, 39, 595. (c) Ganesamoorthy, S.; Sundararajan, G. Macromolecules 1992, 25, 2060. (d) Ganesamoorthy, S.; Sundararajan, G. J. Mol. Catal. 1992, 76, 335.
18. For ETC-catalyzed polymerizations, see: (a) Desbois, M. H.; Astruc, D. J. Chem. Soc., Chem. Commun. 1988, 472. (b) Desbois, M. H.; Astruc, D. New J. Chem. 1989, 39, 595. (c) Ganesamoorthy, S.; Sundararajan, G. Macromolecules 1992, 25, 2060. (d) Ganesamoorthy, S.; Sundararajan, G. J. Mol. Catal. 1992, 76, 335.
19. For example, photochemical as well as electrochemical decomposition of bis(cyclopentadienyl)titanocyclobutane gave a similar product with the same stereochemistry, see: (a) Tamas, W.; Wheeler, D. R.; Grubbs, R. H. J. Am. Chem. Soc. 1987, 109, 6182. (b) Burk, M. J.; Tumas, W.; Ward, M. D.; Wheeler, D. R. J. Am. Chem. Soc. 1990, 112, 6133. (c) Vlcek, A., Jr.; Chemtracts: Inorg. Chem. 1993, 5, 1.
20. For example, photochemical as well as electrochemical decomposition of bis(cyclopentadienyl)titanocyclobutane gave a similar product with the same stereochemistry, see: (a) Tamas, W.; Wheeler, D. R.; Grubbs, R. H. J. Am. Chem. Soc. 1987, 109, 6182. (b) Burk, M. J.; Tumas, W.; Ward, M. D.; Wheeler, D. R. J. Am. Chem. Soc. 1990, 112, 6133. (c) Vlcek, A., Jr.; Chemtracts: Inorg. Chem. 1993, 5, 1.
21. For example, photochemical as well as electrochemical decomposition of bis(cyclopentadienyl)titanocyclobutane gave a similar product with the same stereochemistry, see: (a) Tamas, W.; Wheeler, D. R.; Grubbs, R. H. J. Am. Chem. Soc. 1987, 109, 6182. (b) Burk, M. J.; Tumas, W.; Ward, M. D.; Wheeler, D. R. J. Am. Chem. Soc. 1990, 112, 6133. (c) Vlcek, A., Jr.; Chemtracts: Inorg. Chem. 1993, 5, 1.
22. See ref 5c,d. (a) Shivasubramaniam, V.; Sundararajan, G. J. Mol. Catal. 1991, 65, 205. (b) Vijayaraj, T. A.; Sundararajan, G. J. Mol. Catal. A.: Chem. 1995, 99, 47.
23. See ref 5c,d. (a) Shivasubramaniam, V.; Sundararajan, G. J. Mol. Catal. 1991, 65, 205. (b) Vijayaraj, T. A.; Sundararajan, G. J. Mol. Catal. A.: Chem. 1995, 99, 47.
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25. 3, 0.18.
26. 3, 0.18.
27. 3, 0.18.
28. 3, 0.18.
29. 3, 0.18.
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31. 3 complexes under electrochemical conditions, (c) Lloyd, M. K.; McCleverty, J. A.; Conner, J. A.; Jones, E. M. J. Chem. Soc., Dalton Trans. 1973, 1768. (d) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (e) Meng, Q.; Huang, Y.; Ryan, W. J.; Sweigart, D. A. Inorg. Chem. 1992, 31, 4051. (f) Rourke, F.; Gash, R.; Crayston, J. A. J. Organomet. Chem. 1992, 423, 223.
32. 3 complexes under electrochemical conditions, (c) Lloyd, M. K.; McCleverty, J. A.; Conner, J. A.; Jones, E. M. J. Chem. Soc., Dalton Trans. 1973, 1768. (d) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (e) Meng, Q.; Huang, Y.; Ryan, W. J.; Sweigart, D. A. Inorg. Chem. 1992, 31, 4051. (f) Rourke, F.; Gash, R.; Crayston, J. A. J. Organomet. Chem. 1992, 423, 223.
33. 3 complexes under electrochemical conditions, (c) Lloyd, M. K.; McCleverty, J. A.; Conner, J. A.; Jones, E. M. J. Chem. Soc., Dalton Trans. 1973, 1768. (d) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (e) Meng, Q.; Huang, Y.; Ryan, W. J.; Sweigart, D. A. Inorg. Chem. 1992, 31, 4051. (f) Rourke, F.; Gash, R.; Crayston, J. A. J. Organomet. Chem. 1992, 423, 223.
34. 3 complexes under electrochemical conditions, (c) Lloyd, M. K.; McCleverty, J. A.; Conner, J. A.; Jones, E. M. J. Chem. Soc., Dalton Trans. 1973, 1768. (d) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (e) Meng, Q.; Huang, Y.; Ryan, W. J.; Sweigart, D. A. Inorg. Chem. 1992, 31, 4051. (f) Rourke, F.; Gash, R.; Crayston, J. A. J. Organomet. Chem. 1992, 423, 223.
35. 3 complexes under electrochemical conditions, (c) Lloyd, M. K.; McCleverty, J. A.; Conner, J. A.; Jones, E. M. J. Chem. Soc., Dalton Trans. 1973, 1768. (d) Zhang, Y.; Gosser, D. K.; Rieger, P. H.; Sweigart, D. A. J. Am. Chem. Soc. 1991, 113, 4062. (e) Meng, Q.; Huang, Y.; Ryan, W. J.; Sweigart, D. A. Inorg. Chem. 1992, 31, 4051. (f) Rourke, F.; Gash, R.; Crayston, J. A. J. Organomet. Chem. 1992, 423, 223.
36. 3CN (0).
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44. The reaction mixture was allowed to flow through an IR solution cell fitted with Teflon tubing. The cell was mounted in the IR instrument, and the spectrum was taken at various intervals of time.
45. We are unable to assign this new band to any species.
46. 3 with 1 equiv of chloranil was kept in a refrigerator at 0 °C for 1 week. White crystals were formed in the flask, which were isolated by filtration. The product was identified by various spectral methods and physical constants as 2,3,5,6-tetrachloro-1,4-hydroquinone, the reduced product of chloranil.
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