PM3 Analysis of Nitrone Cycloadditions to Methyl 4,4,4-Trifluoro-2-butenoate

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 8, 1996, Pages 2243-2248

  Tanaka, Kiyoshi ^a   Imase, Tatsuya ^a   Iwata, Satoru ^a  

^a SEIKEI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000556935     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.2243     Document Type: Article

References (25)

1. K. Tanaka, T. Mori, and K. Mitsuhashi, Bull. Chem. Soc. Jpn., 66, 263 (1993); K. Tanaka, T. Mori, and K. Mitsuhashi, Chem. Lett., 1989, 1115.
2. K. Tanaka, T. Mori, and K. Mitsuhashi, Bull. Chem. Soc. Jpn., 66, 263 (1993); K. Tanaka, T. Mori, and K. Mitsuhashi, Chem. Lett., 1989, 1115.
3. J. P. Bégué, D. Bonnet-Delpon, and T. Lequeux, J Chem. Soc., Perkin Trans. 1, 1991, 2888.
4. P. Bravo, L. Bruché, A. Mele, and G. Zecchi, J. Chem. Res., 1991, (S) 81, (M) 719; P. Bravo, L. Bruché, G. Fronza, and G. Zecchi, Tetrahedron, 48, 9775 (1992).
5. P. Bravo, L. Bruché, A. Mele, and G. Zecchi, J. Chem. Res., 1991, (S) 81, (M) 719; P. Bravo, L. Bruché, G. Fronza, and G. Zecchi, Tetrahedron, 48, 9775 (1992).
6. L. W. Boyle, M. J. Peagram, and G. H. Whitham, J. Chem. Soc. B, 1971, 1728.
7. A. Padwa, L. Fisera, K. F. Koehler, A. Rodriguez, and G. S. K. Wong, J. Org. Chem., 49, 276 (1984).
8. A kinetic aspect of this cycloaddtion was reported, see: R. Huisgen, H. Seidl, and I. Bruning, Chem. Ber., 102, 1102 (1969).
9. R. Sustmann, W. Sicking, and R. Huisgen, J. Org. Chem., 58, 82 (1993).
10. T. Matsuoka, K. Harano, and T. Hisano, Heterocycles, 37, 257 (1994).
11. The calculations were carried out by "CAChe MOPAC Ver. 3. 5. 1," J. P. Stewart, QCPE Bull., 9, 10 (1989).
12. R. Huisgen, J. Org. Chem., 41, 403 (1976).
13. K. N. Houk, J. Sims, R. E. Duke, Jr., R. W. Strozier, and J. K. George, J. Am. Chem. Soc., 95, 7287 (1973); K. N. Houk, Acc. Chem. Res., 8, 361 (1975).
14. K. N. Houk, J. Sims, R. E. Duke, Jr., R. W. Strozier, and J. K. George, J. Am. Chem. Soc., 95, 7287 (1973); K. N. Houk, Acc. Chem. Res., 8, 361 (1975).
15. R. Sustmann, Tethahedron Lett., 1971, 2717.
16. J. J. W. McDouall, M. A. Robb, U. Niazi, F. Bernardi, and H. B. Schlegel, J. Am. Chem. Soc., 109, 4642 (1987).
17. M. Joucla and J. Hamelin, J. Chem. Res. M., 1978, 352.
18. J. J. Tufariello," Nitrones," in "1,3-Dipolar Cycloaddition Chemistry," ed by A. Padwa, Wiley Interscience, New York (1984), Chap. 9.
19. B. Gaede and T.M. Balthazor, J. Org. Chem., 48, 276 (1983).
20. Y. Hanzawa, M. Suzuki, Y. Kobayashi, and T. Taguchi, J. Org. Chem., 56, 1718 (1991).
21. S. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, and S. Watanabe, J. Org. Chem., 55, 1736 (1990).
22. "SAPI91", Fan Hai-Fu (1991), Structure analysis programs with intelligent control, Rigaku Corporation, Tokyo, Japan.
23. "DIRDIF92", P. T. Beurskens, G. Admiraal, G. Beurkskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits, and C. Smykalla (1992). The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, Netherlands.
24. "teXsan", Crystal Structure Analysis Package, Molecular Structure Corporation (1985 and 1992),
25. "International Tables for X-Ray Crystallography", Kynoch Press, Birmingham, England (1974), Vol. IV.