Organometallic reactivity on a calix[4]arene oxo surface. The stepwise migratory insertion of carbon monoxide and isocyanides into zirconium-carbon bonds anchored to a calix[4]arene moiety

Journal of the American Chemical Society

Volumn 119, Issue 41, 1997, Pages 9709-9719

  Giannini, Luca ^a   Caselli, Alessandro ^a   Solari, Euro ^a   Floriani, Carlo ^a   Chiesi Villa, Angiola ^b   Rizzoli, Corrado ^b   Re, Nazzareno ^c   Sgamellotti, Antonio ^c  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITY OF PARMA   (Italy)

^c UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CARBON MONOXIDE; ISOCYANATE;

ARTICLE; CHEMICAL BOND; CONFORMATION; DRUG SYNTHESIS; REACTION ANALYSIS; SURFACE PROPERTY; TEMPERATURE;

EID: 0030663291     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9708225     Document Type: Article

References (57)

1. Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, U.K., 1989.
2. (b) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands, 1991.
3. (a) Corker, J.; Lefebvre, F.; Lecuyer, C.; Dufaud, V.; Quignard, F.; Choplin, A.; Evans, J.; Basset, J.-M. Science 1996, 271, 966-969.
4. (b) Niccolai, G. P.; Basset, J.-M. Appl. Catal. A 1996, 146, 145-156.
5. (c) Vidal, V.; Theolier, A.; Thivolle-Cazat, J.; Basset, J.-M.; Corker, J. J. Am. Chem. Soc. 1996, 118, 4595-4662.
6. Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85-87.
7. Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894-4896.
8. (a) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825-2827.
9. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. In press,
10. (c) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491.
11. (d) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035.
12. (e) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371.
13. (f) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
14. (a) Negishi, E.-I.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130 and references therein,
15. (b) Erker, G.; Pfaff, R. Organometallics 1993, 12, 1921-1926.
16. (c) Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; Chapter 3.
17. (d)Negishi, E.-I. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 1163.
18. (e) Schore, N. E. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 1037.
19. (f) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058.
20. (g) Cardin, D. J.; Lappert, M. F.; Raston, C. L. Chemistry of Organozirconium and Hafnium Compounds; Wiley: New York, 1986.
21. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
22. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
23. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
24. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
25. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
26. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
27. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
28. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
29. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
30. Coates, G. W.; Waymouth, R. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 12.1. Ryan, E. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, Chapter 9. Jordan, R. F.; Lapointe, R. E.; Bradley, P. K.; Baenzinger, N. Organometallics 1989, 8, 2892 and references therein. Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895. Neghishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Neghishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407. Neghishi, E.; Yoshida, T. Tetrahedron Lett. 1980, 21, 1501. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Carr, D. B.; Yoshifuji, M.; Shoer, L. I.; Gell, K. I.; Schwartz, J. Ann. N.Y. Acad. Sci. 1977, 295, 127. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
31. Durfee, L. D.; Rothwell, I. P. Chem. Rev. 1988, 88, 1059-1079 and references therein.
32. Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C.; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198.
33. Sheldrick, G. M. SHELX76: Program for Crystal Structure Determination; University of Cambridge: Cambridge, U.K., 1976.
34. Sheldrick, G. SHELXL92: Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1992.
35. (a) Fanwick, P. E.; Kobriger, L. M.; McMullen, A. K.; Rothwell, I. P. J. Am. Chem. Soc. 1986, 108, 8095.
36. (b) Arnold, J.; Tilley, T. D.; Rheingold, A. L. J. Am. Chem. Soc. 1986, 108, 5355.
37. (c) Tatsumi, K.; Nakamura, A.; Hofmann, P.; Stauffert, P.; Hoffmann, R. J. Am. Chem. Soc. 1985, 107, 4440.
38. (d) Martin, B. D.; Matchett, S. A.; Norton, J. R.; Anderson, O. P. J. Am. Chem. Soc. 1985, 107, 7952.
39. (a) Smuck, S.; Erker, G.; Kotila, S. J. Organomet. Chem. 1995, 502, 75-86.
40. (b) Bendix, M.; Grehl, M.; Fröhlich, K.; Erker, G. Organometallics 1994, 13, 3366-3369.
41. (c) Erker, G.; Mena, M.; Krüger, C.; Noe, R. Organometallics 1991, 10, 1201.
42. (d) Erker, G.; Dorf, U.; Czisch, P.; Petersen, J. L. Organometallics 1986, 5, 668. Erker, G.; Czisch, P.; Schlund, R.; Angermund, K.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1986, 15, 364.
43. (d) Erker, G.; Dorf, U.; Czisch, P.; Petersen, J. L. Organometallics 1986, 5, 668. Erker, G.; Czisch, P.; Schlund, R.; Angermund, K.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1986, 15, 364.
44. (a) Valero, C.; Grehl, M.; Wingbermühle, D.; Kloppenburg, L.; Carpenetti, D.; Erker, G.; Petersen. J. Organometallics 1994, 13, 415.
45. (b) Scott, M. J.; Lippard, S. J. J. Am. Chem. Soc. 1997, 119, 3411.
46. (c) Ruiz, J.; Vivanco, M.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1993, 12, 1811-1822 and references therein.
47. Chamberlain, L. R.; Durfee, L. D.; Fanwick, P. E.; Kobriger, L.; Latesky, S. L.; McMullen, A. K.; Rothwell, I. P.; Folting, K.; Huffman, J. C.; Streib, W. E.; Wang, R. J. Am. Chem. Soc. 1987, 109, 390-402.
48. (a) Durfee, L. D.; Hill, J. E.; Kerschner, J. L.; Fanwick, P. E.; Rothwell, I. P. Inorg. Chem. 1989, 28, 3095-6.
49. (b) Durfee, L. D.; Fanwick, P. E.; Rothwell, I. P. Foiling, K.; Huffmann, J. C. J. Am. Chem. Soc. 1987, 109, 4720-2.
50. Chamberlain, L. R.; Durfee, L. D.; Fanwick, P. E.; Kobriger, L. M.; Latesky, S. L.; McMullen, A. K.; Steffey, B. D.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 6068-6076.
51. Latesky, S. L.; McMullen, A. K.; Niccolai, G. P.; Rothwell, I. P. Organometallics 1985, 4, 902.
52. Andreetti, G. D.; Ugozzoli, F. In ref 1b, pp 88-122.
53. Durfee, L. D.; McMullen, A. K.; Rothwell, I. P. J. Am. Chem. Soc. 1988, 110, 1463-1467 and references therein.
54. Hoffmann, R.; Lipscomb, W. N. J. Chem. Phys. 1962, 36, 2179.
55. Hoffmann, R. J. Chem. Phys. 1963, 39, 1397.
56. (a) Tatsumi, K.; Nakamura, A.; Hoffmann, R. Organometallics 1985, 4, 404.
57. (b) Tatsumi, K.; Nakamura, A.; Hofmann, P.; Hoffmann, R.; Moloy, K. G.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 4467.