Novel pi-ligand exchange and insertion reactions involving three- membered phosphorus heterocycles: An ab initio investigation

Journal of the American Chemical Society

Volumn 120, Issue 28, 1998, Pages 7063-7068

  Sølling, Theis I ^a,b   McDonald, Mark A ^a   Wild, S Bruce ^a   Radom, Leo ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ETHYLENE; HYDROCARBON; ION; LIGAND; PHOSPHORUS;

ARTICLE; CALCULATION; CHEMICAL REACTION; ENERGY; PREDICTION; STEREOSPECIFICITY; THEORY;

EID: 0032558080     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980494o     Document Type: Article

References (38)

1. (a) Greenberg, A.; Liebman, J. F. Strained Organic Molecules; Academic Press: New York, 1978.
2. (b) Wiberg, K. Angew. Chem., Int. Ed, Engl. 1986, 25, 312.
3. Wagner, R. I.; Freeman, L. V. D.; Goldwhite, H.; Rowsell, D. G. J. Am. Chem. Soc. 1967, 89, 1102.
4. Mathey, F. Chem. Rev. 1990, 90, 997.
5. Chan, S.; Goldwhite, H.; Keyzer, H.; Rowsell, D. G.; Tang, R. Tetrahedron 1969, 25, 1097.
6. (a) Kang, Y. B.; Pabel, M.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1994, 475.
7. (b) Hockless, D. C. R.; Kang, Y. B.; McDonald, M. A.; Pabel, M.; Willis, A. C.; Wild, S. B. Organometallics 1996, 15, 1301.
8. Li, X.; Robinson, K. D.; Gaspar, P. P. J. Org. Chem. 1996, 61, 7702.
9. Denney, D. B.; Shih, L. S. J. Am. Chem. Soc. 1974, 96, 317.
10. Campbell, B. C.; Denney, D. B.; Denney, D. Z.; Shih, L. S. J. Chem. Soc., Chem. Commun. 1978, 854.
11. Hockless, D. C. R.; McDonald, M. A.; Pabel, M.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 257.
12. Hockless, D. C. R.; McDonald, M. A.; Pabel, M.; Wild, S. B. J. Organomet. Chem. 1997, 529, 189.
13. Vural, J. M.; Weissman, S. A.; Baxter, S. G.; Cowley, A. H.; Nunn, C. M. J. Chem. Soc., Chem. Commun. 1988, 462.
14. McDonald, M. A.; Wild, S. B. Unpublished work.
15. Reed, R. W.; Xie, Z.; Reed, C. A. Organometallics 1995, 14, 5002.
16. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
17. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
18. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
19. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
20. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
21. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
22. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
23. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
24. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
25. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
26. See, for example: (a) Rodriquez, C. F.; Hopkinson, A. C. J. Mol. Struct.: THEOCHEM 1987, 152, 69. (b) Bachrach, J. M. J. Phys. Chem. 1989, 93, 7780. (c) Schoeller, W. W.; Haug, W.; Strutwolf, J. Bull. Soc. Chim. Fr. 1993, 130, 636. (d) Chaquin, P.; Gherbi, A. J. Org. Chem. 1993, 58, 1379. (e) Nguyen, M. T.; Landuyt, L.; Vanquickenborne, L. G. J. Chem. Soc., Faraday Trans. 1994, 90, 1771. (f) Karadakov, P. B.; Gerratt, J.; Cooper, D. L.; Raimondi, M. J. Mol. Struct.: THEOCHEM 1995, 341, 13. (g) Schoeller, W. W.; Tubbesing, U. J. Mol. Struct.: THEOCHEM 1995, 343, 49. (h) Berger, D. J.; Gaspar, P. P.; Liebman, J. F. J. Mol. Struct.: THEOCHEM 1995, 338, 51. (i) Chaquin, P.; Gherbi, A. J. Org. Chem. 1995, 60, 3723. (j) Göller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840. (k) Göller, A.; Heydt, H.; Clark, T. J. Chem. Soc., Chem. Commun. 1997, 1033.
27. Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
28. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94 (rev. E.2); Gaussian, Inc.: Pittsburgh, PA, 1995.
30. MOLPRO 96 is a package of ab initio programs written by H. J. Werner and P. J. Knowles with contributions from J. Almlof, R. D. Amos, M. J. O. Deegan, S. T. Elbert, C. Hempel, W. Meyer, K. Peterson, R. Pitzer, A. J. Stone, P. R. Taylor, and R. Lindh.
31. For recent reviews on G2 theory, see: (a) Curtiss, L. A.; Raghavachari, K. In Quantum Mechanical Electronic Structure Calculations with Chemical Accuracy; Langhoff, S. R., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995. (b) Raghavachari, K.; Curtiss, L. A. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995.
32. For recent reviews on G2 theory, see: (a) Curtiss, L. A.; Raghavachari, K. In Quantum Mechanical Electronic Structure Calculations with Chemical Accuracy; Langhoff, S. R., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995. (b) Raghavachari, K.; Curtiss, L. A. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995.
33. See, for example: (a) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (b) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549.
34. See, for example: (a) Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1993, 115, 4885. (b) Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549.
35. Pople, J. A.; Scott, A. P.; Wong, M. W.; Radom, L. Isr. J. Chem. 1993, 33, 345.
36. Curtiss, L. A.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1995, 103, 4192.
37. Mathey, F. Chem. Rev. 1988, 88, 429.
38. The term "stereospecific" is used to denote a process which is "mechanistically constrained to proceeed in a stereochemically defined manner" as suggested by L. N. Mander in Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994.