Origin of the deactivation in styrene aziridination by aryl azides, catalyzed by ruthenium porphyrin complexes. Structural characterization of a Δ2-1,2,3-triazoline RuII(TPP)CO complex

Organometallics

Volumn 24, Issue 20, 2005, Pages 4710-4713

  Fantauzzi, Simone ^a   Gallo, Emma ^a   Caselli, Alessandro ^a   Ragaini, Fabio ^a   Macchi, Piero ^a   Casati, Nicola ^a   Cenini, Sergio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; ORGANOMETALLICS; PORPHYRINS; REACTION KINETICS; RUTHENIUM COMPOUNDS; STYRENE;

ΑMETHYLSTYRENE; DIANION OF TETRAPHENYLPORPHYRIN (TPP); P-NITROPHENYL AZIDE; STYRENE AZIRIDINATION;

CATALYST DEACTIVATION;

EID: 26444613224     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050244y     Document Type: Article

References (34)

1. (a) Katsuki, T. In Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier: Oxford, U.K., 2004; Vol. 9, pp 207-264.
2. (b) Mueller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919 and references therein.
3. Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem. Eur. J. 2002, 8, 1563-1572.
4. Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C.-M. J. Am. Chem. Soc. 1999, 121, 9120-9132.
5. (a) Cenini, S.; Gallo, E.; Penoni, A.; Ragaini, F.; Tollari, S. Chem. Commun. 2000, 2265-2266.
6. (b) Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Li Gotti, C.; Lapadula, M.; Mangioni, E.; Cenini, S. Chem. Eur. J. 2003, 9, 249-259.
7. Cenini, S.; Tollari, S.; Penoni, A.; Cereda, C. J. Mol. Catal. A: Chem. 1999, 137, 135-146.
8. Since the boiling point of the solvent mixture changes as the fraction of α-methylstyrene increases, all reactions were run at 75°C. Other experimental conditions are as given in the caption to Table 1.
9. Synthesis of 1: p-nitrophenyl azide (100 mg, 0.61 mmol) was dissolved in α-methylstyrene (30 mL). The resulting yellow solution was stirred at 75°C for 28 h, the solvent evaporated in vacuo, and the residue purified by flash chromatography on silica gel (eluent dichloromethane/n-hexane (9/1)) (73%). Recrystallization of the residue from dichloromethane/methanol (1/1) gave crystals of 1 suitable for a structural determination.
10. (a) Kadaba, P. K.; Stanovnik, B.; Tišler, M. Adv. Heterocycl. Chem. 1985, 37, 217-349.
11. (b) Bourgois, J.; Bourgois, M.; Texier, F. Bull. Soc. Chem. Fr. 1978, 9-10, 485-527.
12. (a) Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, U.K., 1984; Vol. 5, pp 669-732.
13. (b) Fan, W. Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 4, pp 1-126.
14. (a) Gieren, A. Chem. Ber. 1973, 106, 288-311.
15. (b) Ferguson, G.; Lough, A. J.; Mackay, D.; Weeratunga, G. J. Chem. Soc., Perkin Trans. 1 1991, 3361-3369.
16. (c) Kaas, K. Acta Crystallogr. 1973, B29, 1458-1463.
17. (d) Mloston, G.; Urbaniak, K.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 2002, 85, 2644-2656.
18. (e) Murata, S.; Mori, Y.; Satoh, Y.; Yoshidome, R.; Tomioka, H. Chem. Lett. 1999, 597-598.
19. (f) Furin, G. G.; Gatilov, Y. V.; Bagryanskay, I. Y.; Zhuzhgov, E. L. J. Fluorine Chem. 2001, 110, 21-24.
20. Hirakawa, K.; Tanabiki, Y. J. Org. Chem. 1982, 47, 280-284.
21. Scheiner, P. Tetrahedron 1968, 24, 2757-2765.
22. Synthesis of 2: 1 (125 mg, 0.44 mmol) was added to a benzene (50 mL) suspension of Ru(TPP)CO (311 mg, 0.42 mmol). The resulting red solution was stirred at 75°C for 15 min and concentrated to 5 mL, and n-hexane (30 mL) was added. The resulting violet solid was collected by filtration, washed with n-hexane, and dried in vacuo (85%). Recrystallization of 2 from ethyl ether gave crystals suitable for a structural determination.
23. Porta, F.; Pizzotti, M.; La Monica, G.; Finessi, L. A.; Cenini, S.; Bellon, P. L.; Demartin, F. J. Chem. Soc., Dalton Trans. 1984, 2409-2414.
24. (a) Kemmerich, T.; Nelson, J. H.; Takach, N. E.; Boehme, H.; Jablonski, B.; Beck, W. Inorg. Chem. 1982, 21, 1226-1232.
25. (b) Paul, P.; Nag, K. Inorg. Chem. 1987, 26, 2969-2974.
26. (c) Guilard, R.; Perrot, I.; Tabard, A.; Richard, P.; Lecomte, C.; Liu, Y. H.; Kadish, K. M. Inorg. Chem. 1991, 30, 27-37.
27. (d) Guilard, R.; Jagerovic, N.; Tabard, A.; Richard, P.; Courthaudon, L.; Louati, A.; Lecomte, C.; Kadish, K. M. Inorg. Chem. 1991, 30, 16-27.
28. (e) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596.
29. Lee, F.-W.; Choi, M.-Y.; Cheung, K.-K.; Che, C.-M. J. Organomet. Chem. 2000, 595, 114-125.
30. Little, R. G.; Ibers, J. A. J. Am. Chem. Soc. 1973, 95, 8583-8590.
31. (a) Scheiner, P. J. Org. Chem. 1965, 30, 7-10.
32. (b) Scheiner, P. J. Am. Chem. Soc. 1966, 88, 4759-4760.
33. (c) Texier, F.; Carrié, R. Bull. Soc. Chem. Fr. 1971, 10, 3642-3648.
34. Omura, K.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Commun. 2004, 2060-2061 and references therein.