Stereoelectronic Effects Characterizing Nucleophilic Carbene Ligands Bound to the Cp*RuCl (Cp* = η5-C5Me5) Moiety: A Structural and Thermochemical Investigation

Organometallics

Volumn 18, Issue 12, 1999, Pages 2370-2375

  Huang, Jinkun ^a   Schanz, Hans Jörg ^a   Stevens, Edwin D ^a   Nolan, Steven P ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000122520     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990054l     Document Type: Article

References (51)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley and Sons: New York, 1994, and references therein,
2. (b) Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993.
3. (a) Pignolet, L. H., Ed. Homogeneous Catalysis with Metal Phosphine Complexes; Plenum: New York, 1983.
4. (b) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; Wiley-Interscience: New York, 1992.
5. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
6. (a) Kubas, G. J. Acc. Chem. Res. 1988, 21, 120-128, and references therein,
7. (b) Gonzales, A. A.; Mukerjee, S. L.; Chou, S.-J.; Zhang, K.; Hoff, C. D. J. Am. Chem. Soc. 1988, 110, 4419-4421.
8. (c) Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9858-9859.
9. (d) Fu G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1983, 115, 9856-9857.
10. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke R. J. Principles and Applications of Organoiransition Metal Chemistry, 2nd ed.; University Science: Mill Valley, CA, 1987.
11. For a short account of the first carbene of this type see: Wanzlick, H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75-80.
12. (a) Hermann, W. A.; Goosen, L. J.; Spiegler, M. J. Organomet. Chem. 1997, 647, 357-366.
13. (b) For a comprehensive review see: Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163-2187.
14. (a) Hermann, W. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 2490-2493.
15. (b) Scholl, M.; Trnka, T. N.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
16. (c) Huang, J.; Stevens, E. D.: Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
17. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. J. Am. Chem. Soc. 1991, 113, 361-363.
18. (a) Arduengo, A. J., III; Gamper, S. F.; Calabreae, J. C.; Davidson, F. J. J. Am. Chem. Soc. 1994, 116, 4391-4393.
19. (b) Adducts of a related carbene ligand with group II and XII metallocenee have been reported: Arduengo, A. J., III; Davidson, F.; Kraftczyk, R.; Marshall, W. J.; Tamm, M. Organometallics 1998, 17, 3375-3382.
20. Arduengo, A. J., III; Dias, H. V. R.; Calabrese, J. C.; Davidsor, F. J. Am. Chem. Soc. 1992, 114, 9724-9725.
21. Campion, B. K.; Heyn, R. H.; Tilley, T. D. Chem. Commun. 1988, 278-280.
22. Fagan, P. J.; Ward, M. D.; Caspar, J. V.; Calabrese, J. C.; Krusic, P. J. J. Am. Chem. Soc. 1988, 110, 2981-2983.
23. Luo, L.; Nolan, S. P. Organometallics 1994, 13, 4781-4786.
24. Solution calorimetric protocol is similar to that previously reported: Serron, S. A.; Huang J.; Nolan, S. P. Organometallics 1998, 17, 534-539.
25. The issue of carbene stability as a function of lone pair steric protection has been recently addressed; see: Arduengo, A. J., III; Krafczyk, R. Chem. Z 1998, 32, 6-14.
26. March, J. Advanced Organic Chemistry; Wiley-Interscience: New York, 1985; pp 242-250.
27. The difference is based on the relative enthalpy values derived from the experimental enthalpies of reaction, as explained in the text.
28. Luo, L.; Nolan, S. P.; Fagan, P. J. Organometallics 1993, 12, 4305-4311.
29. Huang, J.; Haar, C. M.; Nolan, S. P.; Marshall, W. J.; Moloy, K. G. J. Am. Chem. Soc. 1998, 720, 7806-7815.
30. Akitt, J. W. NMR and Chemistry; Chapman and Hall: New-York, 1985.
31. Hydrogen atoms are not considered although it is understood that they will add to the steric bulk of the ligands.
32. Kilday, M. V. J. Res. Natl. Bur. Stand. (U.S.) 1980, 85, 467-481.
33. (a) Nolan, S. P.; Hoff, C. D.; Landrum, J. T. J. Organomet. Chem. 1986, 282, 357-362.
34. (b) Nolan, S. P.; Lopez de la Vega, R.; Hoff, C. D. Inorg. Chem. 1986, 25, 4446-4448.
35. Crociani, B.; Richards, R. L. J. Organomet. Chem. 1978, 144, 85.
36. Key references on metal-assisted alkyne to vinylidene tautomerization include: (a) Werner, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1077. (b) Bianchini, C.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1991, 10, 463. (c) Fryzuk, M. D.; Huang, L.; Mcmanus, N. T.; Paglia, P.; Rettig, S. J.; White, G. S. Organometallics 1992, 11, 2979. (d) Lumprey, J. R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518. (e) Bianchini, C. Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R.; Vacca, A. Organometallics 1996, 14, 3203. (f) de los Ríes, I.; Jiménez Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
37. Key references on metal-assisted alkyne to vinylidene tautomerization include: (a) Werner, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1077. (b) Bianchini, C.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1991, 10, 463. (c) Fryzuk, M. D.; Huang, L.; Mcmanus, N. T.; Paglia, P.; Rettig, S. J.; White, G. S. Organometallics 1992, 11, 2979. (d) Lumprey, J. R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518. (e) Bianchini, C. Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R.; Vacca, A. Organometallics 1996, 14, 3203. (f) de los Ríes, I.; Jiménez Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
38. Key references on metal-assisted alkyne to vinylidene tautomerization include: (a) Werner, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1077. (b) Bianchini, C.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1991, 10, 463. (c) Fryzuk, M. D.; Huang, L.; Mcmanus, N. T.; Paglia, P.; Rettig, S. J.; White, G. S. Organometallics 1992, 11, 2979. (d) Lumprey, J. R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518. (e) Bianchini, C. Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R.; Vacca, A. Organometallics 1996, 14, 3203. (f) de los Ríes, I.; Jiménez Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
39. Key references on metal-assisted alkyne to vinylidene tautomerization include: (a) Werner, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1077. (b) Bianchini, C.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1991, 10, 463. (c) Fryzuk, M. D.; Huang, L.; Mcmanus, N. T.; Paglia, P.; Rettig, S. J.; White, G. S. Organometallics 1992, 11, 2979. (d) Lumprey, J. R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518. (e) Bianchini, C. Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R.; Vacca, A. Organometallics 1996, 14, 3203. (f) de los Ríes, I.; Jiménez Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
40. Key references on metal-assisted alkyne to vinylidene tautomerization include: (a) Werner, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1077. (b) Bianchini, C.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1991, 10, 463. (c) Fryzuk, M. D.; Huang, L.; Mcmanus, N. T.; Paglia, P.; Rettig, S. J.; White, G. S. Organometallics 1992, 11, 2979. (d) Lumprey, J. R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518. (e) Bianchini, C. Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R.; Vacca, A. Organometallics 1996, 14, 3203. (f) de los Ríes, I.; Jiménez Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
41. Key references on metal-assisted alkyne to vinylidene tautomerization include: (a) Werner, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1077. (b) Bianchini, C.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1991, 10, 463. (c) Fryzuk, M. D.; Huang, L.; Mcmanus, N. T.; Paglia, P.; Rettig, S. J.; White, G. S. Organometallics 1992, 11, 2979. (d) Lumprey, J. R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518. (e) Bianchini, C. Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R.; Vacca, A. Organometallics 1996, 14, 3203. (f) de los Ríes, I.; Jiménez Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
42. Bianchini, C.; Farnetti, E.; Glendenning, L.; Graziani, M.; Nardin, G.; Peruzzini, M.; Rocchini, E.; Zanobini, F. Organometallics 1995, 14, 1489.
43. Bianchini, C.; Peruzzini, M.; Purches, G.; Zanobini, F. Inorg. Chim. Acta 1998, 272, 1.
44. (a) Conejo, M. d. M.; Pizzarro, A.; Śnchez, L. J.; Carmona, E. J. Chem. Soc., Dalton Trans. 1996, 3687.
45. (b) Stark, G. A.; Gladysz, J. A. Inorg. Chem. 1996, 35, 5509.
46. (c) Delis, J. G. P.; Aubel, P. G.; van Leeuwen, P. W. N. M.; Vrieze, K.; Veldman, N.; Spek, A. L. J. Chem. Soc., Chem. Commun. 1996, 2233.
47. The addition of amine across alkyne triple bonds gives enamines that, similarly to enols, tautomerize to the more stable imines. No rearrangement of imine to nitrile or isonitriles has ever been reported, however
48. Barrett, A. G. M.; Carpenter, N. E.; Sabat, M. J. Organomet. Chem. 1988, 352, C8.
49. For a review, see: (a) Chekulaeva, B.; Kondrat'eva, D. Russ. Chem. Rev. (Engl. Transl.) 1965, 34, 669. (b) Dickstein, J. I.; Miller, S. I. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, U.K., 1978; Vol. 24, Chapter 19.
50. For a review, see: (a) Chekulaeva, B.; Kondrat'eva, D. Russ. Chem. Rev. (Engl. Transl.) 1965, 34, 669. (b) Dickstein, J. I.; Miller, S. I. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: Chichester, U.K., 1978; Vol. 24, Chapter 19.
51. Brunner, H.; Vogel, M. J. Organomet. Chem. 1972, 35, 169.