Intramolecular cyclization of dinitriles via zirconocene(IV)-phosphorus exchange reactions: Synthesis of σ3,λ3-1-phospha- and σ3,λ3-1,4-diphospha-2,6-diazines

Organometallics

Volumn 18, Issue 16, 1999, Pages 3138-3141

  Maraval, Alexandrine ^a   Donnadieu, Bruno ^a   Igau, Alain ^a   Majoral, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000153621     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990297d     Document Type: Article

References (40)

1. For recent reviews for general survey, see: Qjima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. Lautens, M.; Klute, W.; Tam, W. Ibid. 1996, 96, 49. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. For reviews on early transition metal-mediated cyclization, see: Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Sato, F.; Urabe, H. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996; p 23.
2. For recent reviews for general survey, see: Qjima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. Lautens, M.; Klute, W.; Tam, W. Ibid. 1996, 96, 49. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. For reviews on early transition metal-mediated cyclization, see: Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Sato, F.; Urabe, H. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996; p 23.
3. For recent reviews for general survey, see: Qjima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. Lautens, M.; Klute, W.; Tam, W. Ibid. 1996, 96, 49. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. For reviews on early transition metal-mediated cyclization, see: Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Sato, F.; Urabe, H. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996; p 23.
4. For recent reviews for general survey, see: Qjima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. Lautens, M.; Klute, W.; Tam, W. Ibid. 1996, 96, 49. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. For reviews on early transition metal-mediated cyclization, see: Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Sato, F.; Urabe, H. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996; p 23.
5. For recent reviews for general survey, see: Qjima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. Lautens, M.; Klute, W.; Tam, W. Ibid. 1996, 96, 49. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. For reviews on early transition metal-mediated cyclization, see: Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Sato, F.; Urabe, H. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996; p 23.
6. For recent reviews for general survey, see: Qjima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. Lautens, M.; Klute, W.; Tam, W. Ibid. 1996, 96, 49. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. For reviews on early transition metal-mediated cyclization, see: Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 1163. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Sato, F.; Urabe, H. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996; p 23.
7. Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310.
8. Some examples of nitrile coupling reactions have been reported: Bercaw, J. E.; Davies, D. L.; Wolczanski, P. T. Organometallics 1986, 5, 443.
9. Richeson, D. S.; Mitchell, J. F.; Theopold, K. H. J. Am. Chem. Soc. 1987, 119, 5868.
10. Doxsee, K. M.; Farahi, J. B. J. Am. Chem. Soc. 1988, 110, 7239.
11. Doxsee, K. M.; Farahi, J. B.; Hope, H. J. Am. Chem. Soc. 1991, 113, 8889.
12. Zablocka, M.; Igau, A.; Cénac, N.; Donnadieu, B.; Dahan, F.; Majoral, J. P.; Pietrusiewicz, M. J. Am. Chem. Soc. 1995, 117, 8083. Cénac, N.; Zablocka, M.; Igau, A.; Commenges, G.; Majoral, J P.; Skowronska, A. Organometallics 1996, 15, 1208. Dupuis, L.; Pirio, N.; Meunier, P.; Igau, A.; Donnadieu, B.; Majoral, J.-P. Angew. Chem., Int. Ed. Engl. 1997, 36, 987. For review, see: Majoral, J. P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879. Majoral, J. P.; Meunier, P.; Igau, A.; Pirio, N.; Zablocka, M.; Skowronska, A.; Bredeau, S. Coord. Chem. Rev. 1998, 178-180, 145. Majoral, J. P.; Igau, A. Coord. Chem. Rev. 1998, 176, 1
13. Zablocka, M.; Igau, A.; Cénac, N.; Donnadieu, B.; Dahan, F.; Majoral, J. P.; Pietrusiewicz, M. J. Am. Chem. Soc. 1995, 117, 8083. Cénac, N.; Zablocka, M.; Igau, A.; Commenges, G.; Majoral, J P.; Skowronska, A. Organometallics 1996, 15, 1208. Dupuis, L.; Pirio, N.; Meunier, P.; Igau, A.; Donnadieu, B.; Majoral, J.-P. Angew. Chem., Int. Ed. Engl. 1997, 36, 987. For review, see: Majoral, J. P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879. Majoral, J. P.; Meunier, P.; Igau, A.; Pirio, N.; Zablocka, M.; Skowronska, A.; Bredeau, S. Coord. Chem. Rev. 1998, 178-180, 145. Majoral, J. P.; Igau, A. Coord. Chem. Rev. 1998, 176, 1
14. Zablocka, M.; Igau, A.; Cénac, N.; Donnadieu, B.; Dahan, F.; Majoral, J. P.; Pietrusiewicz, M. J. Am. Chem. Soc. 1995, 117, 8083. Cénac, N.; Zablocka, M.; Igau, A.; Commenges, G.; Majoral, J P.; Skowronska, A. Organometallics 1996, 15, 1208. Dupuis, L.; Pirio, N.; Meunier, P.; Igau, A.; Donnadieu, B.; Majoral, J.-P. Angew. Chem., Int. Ed. Engl. 1997, 36, 987. For review, see: Majoral, J. P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879. Majoral, J. P.; Meunier, P.; Igau, A.; Pirio, N.; Zablocka, M.; Skowronska, A.; Bredeau, S. Coord. Chem. Rev. 1998, 178-180, 145. Majoral, J. P.; Igau, A. Coord. Chem. Rev. 1998, 176, 1
15. Zablocka, M.; Igau, A.; Cénac, N.; Donnadieu, B.; Dahan, F.; Majoral, J. P.; Pietrusiewicz, M. J. Am. Chem. Soc. 1995, 117, 8083. Cénac, N.; Zablocka, M.; Igau, A.; Commenges, G.; Majoral, J P.; Skowronska, A. Organometallics 1996, 15, 1208. Dupuis, L.; Pirio, N.; Meunier, P.; Igau, A.; Donnadieu, B.; Majoral, J.-P. Angew. Chem., Int. Ed. Engl. 1997, 36, 987. For review, see: Majoral, J. P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879. Majoral, J. P.; Meunier, P.; Igau, A.; Pirio, N.; Zablocka, M.; Skowronska, A.; Bredeau, S. Coord. Chem. Rev. 1998, 178-180, 145. Majoral, J. P.; Igau, A. Coord. Chem. Rev. 1998, 176, 1
16. Zablocka, M.; Igau, A.; Cénac, N.; Donnadieu, B.; Dahan, F.; Majoral, J. P.; Pietrusiewicz, M. J. Am. Chem. Soc. 1995, 117, 8083. Cénac, N.; Zablocka, M.; Igau, A.; Commenges, G.; Majoral, J P.; Skowronska, A. Organometallics 1996, 15, 1208. Dupuis, L.; Pirio, N.; Meunier, P.; Igau, A.; Donnadieu, B.; Majoral, J.-P. Angew. Chem., Int. Ed. Engl. 1997, 36, 987. For review, see: Majoral, J. P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879. Majoral, J. P.; Meunier, P.; Igau, A.; Pirio, N.; Zablocka, M.; Skowronska, A.; Bredeau, S. Coord. Chem. Rev. 1998, 178-180, 145. Majoral, J. P.; Igau, A. Coord. Chem. Rev. 1998, 176, 1
17. Zablocka, M.; Igau, A.; Cénac, N.; Donnadieu, B.; Dahan, F.; Majoral, J. P.; Pietrusiewicz, M. J. Am. Chem. Soc. 1995, 117, 8083. Cénac, N.; Zablocka, M.; Igau, A.; Commenges, G.; Majoral, J P.; Skowronska, A. Organometallics 1996, 15, 1208. Dupuis, L.; Pirio, N.; Meunier, P.; Igau, A.; Donnadieu, B.; Majoral, J.-P. Angew. Chem., Int. Ed. Engl. 1997, 36, 987. For review, see: Majoral, J. P.; Zablocka, M.; Igau, A.; Cénac, N. Chem. Ber. 1996, 129, 879. Majoral, J. P.; Meunier, P.; Igau, A.; Pirio, N.; Zablocka, M.; Skowronska, A.; Bredeau, S. Coord. Chem. Rev. 1998, 178-180, 145. Majoral, J. P.; Igau, A. Coord. Chem. Rev. 1998, 176, 1
18. Bodor, N. In Design of Biopharmaceutical Properties Through Prodrugs and Analogs; Roche, E. B., Ed.; American Pharmaceutical Associations: Washington, DC, 1977; p 98. Stone, H. P. J. Cardiovasc. Med. 1982, 7, 181. Baba, N.; Amano, M.; Oda, J.; Inouye, Y. J. Am. Chem. Soc. 1984, 106, 1481, and references therein.
19. Bodor, N. In Design of Biopharmaceutical Properties Through Prodrugs and Analogs; Roche, E. B., Ed.; American Pharmaceutical Associations: Washington, DC, 1977; p 98. Stone, H. P. J. Cardiovasc. Med. 1982, 7, 181. Baba, N.; Amano, M.; Oda, J.; Inouye, Y. J. Am. Chem. Soc. 1984, 106, 1481, and references therein.
20. Bodor, N. In Design of Biopharmaceutical Properties Through Prodrugs and Analogs; Roche, E. B., Ed.; American Pharmaceutical Associations: Washington, DC, 1977; p 98. Stone, H. P. J. Cardiovasc. Med. 1982, 7, 181. Baba, N.; Amano, M.; Oda, J.; Inouye, Y. J. Am. Chem. Soc. 1984, 106, 1481, and references therein.
21. Daley, S. T. A.; Rees, C. W.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 57. Weidenbruch, M.; Schäfer, A. J. Organomet. Chem. 1986, 314, 25. Sundermeyer, J.; Roesky, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 609. Butler, R. N.; Evans, A. M.; McNeela, E. M.; O'Halloran, G. A.; O'Shea, P. D.; Cunningham, D.; McArdle, P. J. Chem. Soc., Perkin Trans. 1990, 2527. Yonemoto, K.; Shibuya, I., Tsuchiya, T.; Yasumoto, M.; Taguchi, Y. Bull. Chem. Soc. Jpn. 1990, 63, 2933. Weidenbruch, M.; Will, P.; Peters, K.; von Schnering, H. G.; Marsmann, H. J. Organomet. Chem. 1996, 521, 355.
22. Daley, S. T. A.; Rees, C. W.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 57. Weidenbruch, M.; Schäfer, A. J. Organomet. Chem. 1986, 314, 25. Sundermeyer, J.; Roesky, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 609. Butler, R. N.; Evans, A. M.; McNeela, E. M.; O'Halloran, G. A.; O'Shea, P. D.; Cunningham, D.; McArdle, P. J. Chem. Soc., Perkin Trans. 1990, 2527. Yonemoto, K.; Shibuya, I., Tsuchiya, T.; Yasumoto, M.; Taguchi, Y. Bull. Chem. Soc. Jpn. 1990, 63, 2933. Weidenbruch, M.; Will, P.; Peters, K.; von Schnering, H. G.; Marsmann, H. J. Organomet. Chem. 1996, 521, 355.
23. Daley, S. T. A.; Rees, C. W.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 57. Weidenbruch, M.; Schäfer, A. J. Organomet. Chem. 1986, 314, 25. Sundermeyer, J.; Roesky, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 609. Butler, R. N.; Evans, A. M.; McNeela, E. M.; O'Halloran, G. A.; O'Shea, P. D.; Cunningham, D.; McArdle, P. J. Chem. Soc., Perkin Trans. 1990, 2527. Yonemoto, K.; Shibuya, I., Tsuchiya, T.; Yasumoto, M.; Taguchi, Y. Bull. Chem. Soc. Jpn. 1990, 63, 2933. Weidenbruch, M.; Will, P.; Peters, K.; von Schnering, H. G.; Marsmann, H. J. Organomet. Chem. 1996, 521, 355.
24. Daley, S. T. A.; Rees, C. W.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 57. Weidenbruch, M.; Schäfer, A. J. Organomet. Chem. 1986, 314, 25. Sundermeyer, J.; Roesky, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 609. Butler, R. N.; Evans, A. M.; McNeela, E. M.; O'Halloran, G. A.; O'Shea, P. D.; Cunningham, D.; McArdle, P. J. Chem. Soc., Perkin Trans. 1990, 2527. Yonemoto, K.; Shibuya, I., Tsuchiya, T.; Yasumoto, M.; Taguchi, Y. Bull. Chem. Soc. Jpn. 1990, 63, 2933. Weidenbruch, M.; Will, P.; Peters, K.; von Schnering, H. G.; Marsmann, H. J. Organomet. Chem. 1996, 521, 355.
25. Daley, S. T. A.; Rees, C. W.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 57. Weidenbruch, M.; Schäfer, A. J. Organomet. Chem. 1986, 314, 25. Sundermeyer, J.; Roesky, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 609. Butler, R. N.; Evans, A. M.; McNeela, E. M.; O'Halloran, G. A.; O'Shea, P. D.; Cunningham, D.; McArdle, P. J. Chem. Soc., Perkin Trans. 1990, 2527. Yonemoto, K.; Shibuya, I., Tsuchiya, T.; Yasumoto, M.; Taguchi, Y. Bull. Chem. Soc. Jpn. 1990, 63, 2933. Weidenbruch, M.; Will, P.; Peters, K.; von Schnering, H. G.; Marsmann, H. J. Organomet. Chem. 1996, 521, 355.
26. Daley, S. T. A.; Rees, C. W.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 57. Weidenbruch, M.; Schäfer, A. J. Organomet. Chem. 1986, 314, 25. Sundermeyer, J.; Roesky, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 609. Butler, R. N.; Evans, A. M.; McNeela, E. M.; O'Halloran, G. A.; O'Shea, P. D.; Cunningham, D.; McArdle, P. J. Chem. Soc., Perkin Trans. 1990, 2527. Yonemoto, K.; Shibuya, I., Tsuchiya, T.; Yasumoto, M.; Taguchi, Y. Bull. Chem. Soc. Jpn. 1990, 63, 2933. Weidenbruch, M.; Will, P.; Peters, K.; von Schnering, H. G.; Marsmann, H. J. Organomet. Chem. 1996, 521, 355.
27. Bishydrozirconation on dinitrile derivatives was not reported before this work. For hydrozirconation on nitriles see for example: Erker, G.; Frömberg, W.; Atwood, J. L.; Hunter, W. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 68. Boutonnet, F.; Dufour, N.; Straw, T.; Igau, A.; Majoral, J.-P. Organometallics 1991, 10, 3939.
28. Bishydrozirconation on dinitrile derivatives was not reported before this work. For hydrozirconation on nitriles see for example: Erker, G.; Frömberg, W.; Atwood, J. L.; Hunter, W. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 68. Boutonnet, F.; Dufour, N.; Straw, T.; Igau, A.; Majoral, J.-P. Organometallics 1991, 10, 3939.
29. Exchange reactions involving zirconocene complexes with Zr-C bonds and various main group elements are known; see for example ref 2, and: Breen, T. L.; Stephan, D. W. Organometallics 1997, 16, 365, and references therein. However none of the reactions involve a transmetalation/cyclization from bis(aldimido) complexes incorporating two independent Zr-N bonds.
30. See for example: Bochmann, M.; Wilson, L. M. J. Chem. Soc., Chem. Commun. 1986, 1610. Jordan, R. F.; Bajgur, C. S.; Dasher, W. E. Organometallics 1987, 6, 1041.
31. See for example: Bochmann, M.; Wilson, L. M. J. Chem. Soc., Chem. Commun. 1986, 1610. Jordan, R. F.; Bajgur, C. S.; Dasher, W. E. Organometallics 1987, 6, 1041.
32. 2) on an iminophosphine P=N double bond has already been reported: Larré, C.; Mahieu, A.; Igau, A.; Majoral, J.-P. J. Organomet. Chem. 1995, 493, 133.
33. Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
34. Niecke, E.; Nieger, M.; Reichert, F. Angew. Chem., Int. Ed. Engl. 1988, 12, 1715.
35. Altomare, A.; Cascarano, G.; Giacovazzo, G.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. SIR92, a program for automatic solution of crystal structures by direct methods. J. Appl. Crystallogr. 1994, 27, 435.
36. Flack, H. Acta Crystallogr. 1983, A39, 876.
37. Carruthers, J. R.; Watkin, D. J. Acta Crystallogr. 1979, A35, 698.
38. Watkin, D. J.; Prout, C. K.; Carruthers, R. J.; Betteridge, P. CRYSTALS. Chemical Crystallography Laboratory: Oxford, U.K., 1996; Issue 10.
39. Watkin, D. J.; Prout, C. K.; Pearce, L. J. CAMERON. Chemical Crystallography Laboratory,: Oxford, U.K., 1996.
40. International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol IV.