Facile alkylation of cobalt(III) porphyrins by organosilicon compounds

Organometallics

Volumn 16, Issue 16, 1997, Pages 3679-3683

  Watanabe, Jun Ya ^a   Setsune, Jun Ichiro ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000158169     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970174y     Document Type: Article

References (36)

1. (a) Clarke, D. A.; Dolphin, D.; Grigg, R.; Johnson, A. W.; Pinnock, H. A. J. Chem. Soc. 1968, 881.
2. (b) Schrauzer, G. N. Angew. Chem. 1976, 88, 465.
3. (c) Dodd, D.; Johnson, M. D. J. Organomet. Chem. 1973, 52, 1.
4. (d) Perree-Fauvet, M.; Gaudemer, A.; Boucly, P.; Devynck, J. J. Organomet. Chem. 1976, 120, 439.
5. (e) Ogoshi, H.; Watanabe, E.; Koketsu, N.; Yoshida, Z. Bull. Chem. Soc. Jpn. 1976, 49, 2529.
6. (a) Silverman, R. B.; Dolphin, D. J. Am. Chem. Soc. 1976, 98, 4626.
7. (b) Sugimoto, H.; Ueda, N.; Mori, M. Bull. Chem. Soc. Jpn. 1981, 54, 3425.
8. (a) Watanabe, W. H.; Conlon, L. E. J. Am. Chem. Soc. 1957, 79, 2828.
9. (b) Ireland, R. E.; Dawson, D. J. Org. Synth. 1974, 54, 71.
10. (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
11. (b) Paterson, I.; Mcleod, M. Tetrahedron Lett. 1995, 36, 9065.
12. (c) Saraswathy, V.; Sankararaman, S. J. Org. Chem. 1995, 60, 5024.
13. (d) Suzuki, H.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1995, 60, 6114.
14. (e) Tokunoh, R.; Tomiyama, H.; Sodeoka, K.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 2449.
15. (f) Kato, M.; Hasegawa, E. Tetrahedron Lett. 1996, 37, 3483.
16. (g) Karady, S.; Amato, J.; Reamer, R.; Weinstock, L. Tetrahedron Lett. 1996, 37, 8277.
17. (h) Rathove, R.; Kochi, J. J. Org. Chem. 1996, 61, 627.
18. (i) Zoretic, P.; Wang, M.; Zhang, Y.; Shen, Z.; Ribeiro, A. J. Org. Chem. 1996, 61, 1806.
19. (j) Padwa, A.; Brodney, M.; Marino, J.; Sheehan, S. J. Org. Chem. 1997, 62, 78.
20. (k) Bergmeiyer, S.; Seth, P. Tetrahedron Lett. 1995, 36, 3793.
21. (l) Osumi, K.; Sugimura, H. Tetrahedron Lett. 1995, 36, 5789.
22. (m) Linderman, R.; Chen, K. J. Org. Chem. 1996, 61, 2441.
23. (n) Horiuchi, Y.; Oshima, K.; Utimoto, K. J. Org. Chem. 1996, 61, 4483.
24. (o) Asao, N.; Yoshikawa, E.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4874.
25. (p) Ofial, A.; Mayr, H. J. Org. Chem. 1996, 61, 5823.
26. (a) Setsune, J.; Watanabe, J. Chem. Lett. 1994, 2253.
27. (b) Ogoshi, H.; Setsune, J.; Nanbo, Y.; Yoshida, Z. J. Organomet. Chem. 1978, 159, 329.
28. Arasasingham, R. D.; Balch, A. L.; Cornman, C. R.; Latos-Grazynski, L. J. Am. Chem. Soc. 1989, 111, 4357.
29. Kendrick, M. J.; Al-Akhbar, W. Inorg. Chem. 1987, 26, 3972.
30. Cooksey, C. J.; Dodd, D.; Gatford, C.; Johnson, M. D.; Lewis, G. J.; Titchmarsh, D. M. J. Chem. Soc., Perkin Trans. 2 1972, 655.
31. (a) Dodd, D.; Johnson, M. D. J. Am. Chem. Soc. 1974, 96, 2279.
32. (b) Cooksey, C. J.; Dodd, D.; Johnson, M. D.; Lockman, B. L. J. Chem. Soc., Dalton Trans. 1978, 1814.
33. Lide, D. R.; Milne, G. W. A. Handbook of Data on Organic Compounds, 3rd ed.; CRC Press: Boca Raton, FL, 1994; Vol. II.
34. According to the semiempirical MO calculation (see Experimental Section), an energy minimum was observed at the conformation where the dihedral angle 〈Co-C(α)-C(β)-C(γ) is 96.8°. This parallel conformation E is more stable by 5 kcal/mol than the perpendicular conformation F.
35. Fukuzumi, S.; Fujita, M.; Otera, J.; Fujita, Y. J. Am. Chem. Soc. 1992, 114, 10271.
36. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.