An AM1 and DFT-AM1 computational study of methyl phenylpropiolate addition to 1-phenyl-3,4-dimethylphosphole

Journal of Heterocyclic Chemistry

Volumn 33, Issue 4, 1996, Pages 1389-1392

  Jursic, Branko S ^a   LeBlanc, Biaise ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0043220218     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330462     Document Type: Article

References (39)

1. For example see: H. B. Kagan, Comprehensive Organometallic Chemistry, G. Wilkinson, F. G. A. Stone and E. W. Abel, eds, Prgamon press, Oxford, 8, 463 (1982).
2. A. Brèque, J.-M. Alcaraz, L. Ricard, F. Mathey, A. Tambuté and P. Macaudière, New. J. Chem., 13, 369 (1989) and references therein.
3. A. J. Arduengo III, Pure Appl. Chem., 59, 1053 (1987) and references therein.
4. F. Hughes and F. Mercier, Tetrahedron Letters, 22, 319 (1981).
5. A. I. Meyers, Heterocycles in Organic Synthesis, E. C. Tayler and A. Weissberger, eds, John Wiley and Sons, New York, NY, 1974; B. H. Lipshutz, Chem. Rev., 86, 796 (1986); T. Masayoshi and Y. Gosei, Kagaku Kyokaishi, 51, 399 (1993); P. A. Jacobi, K. M. Touchette and H. G. Selnick, J. Org. Chem., 57, 6305 (1992).
6. A. I. Meyers, Heterocycles in Organic Synthesis, E. C. Tayler and A. Weissberger, eds, John Wiley and Sons, New York, NY, 1974; B. H. Lipshutz, Chem. Rev., 86, 796 (1986); T. Masayoshi and Y. Gosei, Kagaku Kyokaishi, 51, 399 (1993); P. A. Jacobi, K. M. Touchette and H. G. Selnick, J. Org. Chem., 57, 6305 (1992).
7. A. I. Meyers, Heterocycles in Organic Synthesis, E. C. Tayler and A. Weissberger, eds, John Wiley and Sons, New York, NY, 1974; B. H. Lipshutz, Chem. Rev., 86, 796 (1986); T. Masayoshi and Y. Gosei, Kagaku Kyokaishi, 51, 399 (1993); P. A. Jacobi, K. M. Touchette and H. G. Selnick, J. Org. Chem., 57, 6305 (1992).
8. A. I. Meyers, Heterocycles in Organic Synthesis, E. C. Tayler and A. Weissberger, eds, John Wiley and Sons, New York, NY, 1974; B. H. Lipshutz, Chem. Rev., 86, 796 (1986); T. Masayoshi and Y. Gosei, Kagaku Kyokaishi, 51, 399 (1993); P. A. Jacobi, K. M. Touchette and H. G. Selnick, J. Org. Chem., 57, 6305 (1992).
9. D. L. Boger and S. N. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, NY, 1987; D. L. Boger, Chem. Rev., 86, 781 (1986); R. R. Schmidt, Acc. Chem. Res., 19, 250 (1986).
10. D. L. Boger and S. N. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, NY, 1987; D. L. Boger, Chem. Rev., 86, 781 (1986); R. R. Schmidt, Acc. Chem. Res., 19, 250 (1986).
11. D. L. Boger and S. N. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, NY, 1987; D. L. Boger, Chem. Rev., 86, 781 (1986); R. R. Schmidt, Acc. Chem. Res., 19, 250 (1986).
12. All calculations were carried out with MOPAC version 6.0. Quantum Chemistry Program Exchange (QCPE), Program Number 455, 1990.
13. The transition state must have only one imaginary frequency. For the transition state theory see: W. J. Albery, Transition-State Theory Revision in Adv. Phys. Org. Chem., 28, 139 (1993); R. A. Marcus, Science, 256, 1523 (1992).
14. The transition state must have only one imaginary frequency. For the transition state theory see: W. J. Albery, Transition-State Theory Revision in Adv. Phys. Org. Chem., 28, 139 (1993); R. A. Marcus, Science, 256, 1523 (1992).
15. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 303, 177 (1994) and references therein.
16. Gaussian 92/DFT, Revision G.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. W. Wong, J. B. Foresman, M. A. Robb, M. Head-Gordon, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1993.
17. For an explanation of GAUSSIAN basis sets see: M. J. Froisch, Æ. Frisch and J. B. Firesman, Gaussian 94 User's Reference, Gaussian, Inc. Pittsburgh, PA, 1994-1995.
18. J. C. Slater, Quantum Theory of Molecular and Solids, Vol 4, The swlf-Consistent Field for Molecular and Solids, McGraw-Hill, New York, 1974.
19. S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys., 58, 1200 (1980).
20. A. D. Becke, J. Chem. Phys., 98, 5648 (1993).
21. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785 (1988).
22. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stevart, J. Am. Chem. Soc., 107, 3902 (1985); M. J. S. Dewar and E. G. Zoebisch, J. Mol. Struc. (Theochem), 180, 1 (1988).
23. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stevart, J. Am. Chem. Soc., 107, 3902 (1985); M. J. S. Dewar and E. G. Zoebisch, J. Mol. Struc. (Theochem), 180, 1 (1988).
24. K. N. Houk, Y.-T. Lin and J. D. Evansek, Angew. Chem., Int. Ed. Engl, 31, 682 (1992) and references therein.
25. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 309, 249 (1994).
26. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 315, 85 (1994); Branko S. Jursic and Z. Zdravkovski, Bull. Chem. Technol Macedonia, 13, 55 (1994); B. S. Jursic and Z. Zdravkovski, J. Heterocyclic Chem., 31, 1429 (1994); B. S. Jursic and D. Coupe, J. Heterocyclic Chem., 32, 483 (1995); B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1217 (1995); B. S. Jursic, J. Heterocyclic Chem., in press; B. S. Jursic, J. Heterocyclic Chem., in press.
27. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 315, 85 (1994); Branko S. Jursic and Z. Zdravkovski, Bull. Chem. Technol Macedonia, 13, 55 (1994); B. S. Jursic and Z. Zdravkovski, J. Heterocyclic Chem., 31, 1429 (1994); B. S. Jursic and D. Coupe, J. Heterocyclic Chem., 32, 483 (1995); B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1217 (1995); B. S. Jursic, J. Heterocyclic Chem., in press; B. S. Jursic, J. Heterocyclic Chem., in press.
28. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 315, 85 (1994); Branko S. Jursic and Z. Zdravkovski, Bull. Chem. Technol Macedonia, 13, 55 (1994); B. S. Jursic and Z. Zdravkovski, J. Heterocyclic Chem., 31, 1429 (1994); B. S. Jursic and D. Coupe, J. Heterocyclic Chem., 32, 483 (1995); B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1217 (1995); B. S. Jursic, J. Heterocyclic Chem., in press; B. S. Jursic, J. Heterocyclic Chem., in press.
29. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 315, 85 (1994); Branko S. Jursic and Z. Zdravkovski, Bull. Chem. Technol Macedonia, 13, 55 (1994); B. S. Jursic and Z. Zdravkovski, J. Heterocyclic Chem., 31, 1429 (1994); B. S. Jursic and D. Coupe, J. Heterocyclic Chem., 32, 483 (1995); B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1217 (1995); B. S. Jursic, J. Heterocyclic Chem., in press; B. S. Jursic, J. Heterocyclic Chem., in press.
30. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 315, 85 (1994); Branko S. Jursic and Z. Zdravkovski, Bull. Chem. Technol Macedonia, 13, 55 (1994); B. S. Jursic and Z. Zdravkovski, J. Heterocyclic Chem., 31, 1429 (1994); B. S. Jursic and D. Coupe, J. Heterocyclic Chem., 32, 483 (1995); B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1217 (1995); B. S. Jursic, J. Heterocyclic Chem., in press; B. S. Jursic, J. Heterocyclic Chem., in press.
31. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 315, 85 (1994); Branko S. Jursic and Z. Zdravkovski, Bull. Chem. Technol Macedonia, 13, 55 (1994); B. S. Jursic and Z. Zdravkovski, J. Heterocyclic Chem., 31, 1429 (1994); B. S. Jursic and D. Coupe, J. Heterocyclic Chem., 32, 483 (1995); B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1217 (1995); B. S. Jursic, J. Heterocyclic Chem., in press; B. S. Jursic, J. Heterocyclic Chem., in press.
32. B. S. Jursic and Z. Zdravkovski, J. Mol. Struc. (Theochem), 315, 85 (1994); Branko S. Jursic and Z. Zdravkovski, Bull. Chem. Technol Macedonia, 13, 55 (1994); B. S. Jursic and Z. Zdravkovski, J. Heterocyclic Chem., 31, 1429 (1994); B. S. Jursic and D. Coupe, J. Heterocyclic Chem., 32, 483 (1995); B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1217 (1995); B. S. Jursic, J. Heterocyclic Chem., in press; B. S. Jursic, J. Heterocyclic Chem., in press.
33. K. Houk, J. Gonzalez and Y. Li, Acc. Chem. Res., 28, 81 (1995) and references therein.
34. B. S. Jursic and Z. Zdravkovski, J. Chem. Soc., Perkin Trans. 2, 1223 (1995)
35. For application of DFT methods to chemical problems of interes see: J. M. Seminario and P. Politzer, eds, Modern Density Functional Theory A Tool for Chemistry, Elsevier, Amsterdam, 1995.
36. B. S. Jursic, J. Mol. Struc. (Theochem), in press.
37. B. S. Jursic, J. Chem. Soc., Perkin Trans 2, in press.
38. B. S. Jursic, J. Comp. Chem., in press; B. S. Jursic, manuscript in preparation.
39. B. S. Jursic, J. Comp. Chem., in press; B. S. Jursic, manuscript in preparation.