1,3-Dipolar cycloadditions of thionitroso compounds (R-N=S): A density functional theory study

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 6, 1999, Pages 1249-1255

  Le, Trung Ngoc ^a   Nguyen, Loc Thanh ^a   Chandra, Asit K ^b   De Proft, Frank ^a   Geerlings, Paul ^a   Nguyen, Minh Tho ^b  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000804278     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806687f     Document Type: Article

References (50)

1. D. L. Boger and S. M. Weinveb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, Orlando, 1987.
2. M. R. Bryce, J. Becher and B. Falt-Hansen, Adv. Heterocycl. Chem., 1992, 55, 1.
3. L. Fisera, R. Huisgen, I. Kalwinsch, E. Langhels, X. Li, G. Mloston, K. Polborn, J. Rapp, W. Sicking and R. Sustman, Pure Appl. Chem., 1996, 68, 789.
4. M. Takabashi, R. Okazaki, Sulfur Rep., 1993, 13, 293.
5. M. Takabashi, R. Okazaki and N. Inamoto, Chem. Lett., 1989, 2087.
6. M. Takabashi, R. Okazaki, N. Inamoto, T. Sugawara and H. Iwamura, J. Am. Chem. Soc., 1992, 114, 1830.
7. M. R. Bryce and P. C. Taylor, J. Chem. Soc., Perkin Trans. 1, 1990, 3225.
8. M. R. Bryce, A. Chesney, G. N. Mckelvey, A. S. Batsanov, J. A. K. Howard and M. Anderson, J. Chem. Soc., Perkin Trans. 1, 1996, 1825.
9. C. Diaz, E. Benavente and G. Gonzalez, Phosphorous Sulfur Silicon, 1995, 101, 37.
10. M. T. Nguyen, A. W. Allaf, R. Flammang and Y. Van Haverbeke, THEOCHEM, 1997, 418, 209.
11. M. T. Nguyen, L. G. Vanquickenborne and R. Flammang, J. Chem. Phys. , 1994, 101, 4885.
12. R. G Parr and W. Yang, Annu. Rev. Phys. Chem., 1995, 46, 701.
13. P. Geerlings, F. De Proft and W. Langenaeker, Adv. Quantum Chem., 1999, 33, 303.
14. A. K. Chandra, P. Geerlings and M. T. Nguyen, J. Org. Chem., 1997, 62, 6417.
15. D. Sengupta, A. K. Chandra and M. T. Nguyen, J. Org. Chem., 1997, 62, 6404.
16. A. K. Chandra and M. T. Nguyen, J. Comput. Chem., 1998, 19, 195.
17. S. Damoun, G. Van de Woude, F. Mendez and P. Geerlings, J. Phys. Chem., 1997, 101, 886.
18. R. G. Pearson, Acc. Chem. Res., 1993, 26, 250.
19. Gaussian 94, Revision C.3, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995.
20. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
21. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785.
22. J. J. W. McDowell, M. A. Robb, U. Niazi, F. Bernardi and H. B. Schelegel, J. Am. Chem. Soc., 1987, 109, 4642.
23. C. Sosa, J. Andzelm, C. Lee, J. G. Blake, B. C. Chenard and J. W. Buther, Int. J. Quantum Chem., 1994, 49, 511.
24. M. Breneman and K. Wiberg, J. Comput. Chem., 1990, 11, 361.
25. P. Geerlings, F. De Proft and J. M. L. Martin, in Recent Developments in Density Functional Theory, ed. J. Seminario, Elsevier, Amsterdam, 1996, p. 773.
26. W. J. Middleton, J. Am. Chem. Soc., 1966, 88, 3842.
27. H. W. Roesley, R. Emmert, W. Isaberg, M. Schmidt and G. M. Scheldrick, J. Chem. Soc., Dalton Trans., 1983, 183.
28. G. Leroy, M. Sana, L. A. Burke and M. T. Nguyen, Quantum Theory of Chemical Reactions, Reidel, 1979, vol. 1, pp. 91-144.
29. M. T. Nguyen, THEOCHEM, 1983, 105, 343.
30. M. Regitz, Chem. Rev., 1990, 90, 191.
31. L. Nyulaszi, P. Varnai, W. Eisfeld and M. Regitz, J. Comput. Chem., 1997, 18, 609.
32. R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
33. R. G. Pearson, Coord. Chem. Rev., 1990, 100, 403. For recent reviews, see: Chemical Hardness, Structure and Bonding, ed. K. D. Sen, Springer-Verlag, Berlin, 1993, vol. 80.
34. R. G. Pearson, Coord. Chem. Rev., 1990, 100, 403. For recent reviews, see: Chemical Hardness, Structure and Bonding, ed. K. D. Sen, Springer-Verlag, Berlin, 1993, vol. 80.
35. R. G. Pearson and R. G. Parr, J. Am. Chem. Soc., 1983, 105, 7512.
36. W. Yang and W. J. Mortier, J. Am. Chem. Soc., 1986, 108, 5708.
37. J. L. Gazquez and F. Mendez, J. Phys. Chem., 1994, 98, 4591.
38. F. Mendez, J. Tamariz and P. Geerlings, J. Phys. Chem. A, 1998, 102, 6292.
39. A. Rastelli, R. Gandolfi and M. S. Amade, J. Org. Chem., 1998, 63, 7425.
40. H. D. Cohen and C. C. J. Roothan, J. Chem. Phys., 1965, 43, S34.
41. A. K. Chandra and M. T. Nguyen, J. Phys. Chem., 1998, 102, 6181.
42. P. Politzer, J. S. Murray and M. Edward Grice, Chemical Hardness, Structure and Bonding, Springer-Verlag, Berlin, 1993, vol. 80.
43. T. Ghanty and S. K. Ghosh, J. Phys. Chem., 1993, 97, 4951.
44. T. Ghanty and S. K. Ghosh, J. Phys. Chem., 1996, 100, 12295.
45. S. Pal and A. K. Chandra, J. Phys. Chem., 1995, 99, 13865.
46. P. K. Chattaraj and S. Sengupta, J. Phys. Chem., 1997, 101, 7893.
47. D. Datta, J. Phys. Chem., 1992, 96, 2409.
48. P. K. Chattaraj, S. Nath and A. B. Sannigrahi, J. Phys. Chem., 1994, 98, 9143.
49. J. I. Cardenas-Jiron and A. Toro-Labbe, J. Phys. Chem., 1995, 99, 5325.
50. J. I. Cardenas-Jiron, S. Gutirrez-Oliva, J. Melin and A. Toro-Labbe, J. Phys. Chem., 1997, 101, 4621.