Theoretical study of the [2+2] cycloaddition of thioketenes with imines to form β-thiolactams

Chemistry - A European Journal

Volumn 4, Issue 2, 1998, Pages 328-334

  López, Ramón ^a   Suárez, Dimas ^a   Sordo, Tomás L ^a   Ruiz López, Manuel F ^b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b NANCY UNIVERSITÉ   (France)

Author keywords

Ab initio calculations; Cycloadditions; Lactams; Solvent effects; Torquoelectronic effects

Indexed keywords

EID: 0345019906     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980210)4:2<328::AID-CHEM328>3.0.CO;2-Q     Document Type: Article

References (34)

1. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Elmsford, N.Y. 1990.
2. a) D. Bellus, B. Ernst, Angew. Chem. 1988, 100, 820-850; Angew. Chem. Int. Ed. Engl. 1988, 27, 797-827;
3. a) D. Bellus, B. Ernst, Angew. Chem. 1988, 100, 820-850; Angew. Chem. Int. Ed. Engl. 1988, 27, 797-827;
4. b) B.B. Snider, Chem. Rev. 1988, 88, 793-811;
5. c) G. I. Georg, V.T. Ravikumar, in The Organic Chemistry of β-Lactams (Ed.: G. I. Georg), VCH, New York, 1993.
6. E. Schaumann, Chem. Ber. 1976, 109, 906-921.
7. X. Creary, C. Zhu, J. Am. Chem. Soc. 1995, 117, 5859-5860.
8. a) J. A. Sordo, J. González, T. L. Sordo, J. Am. Chem. Soc. 1992, 114, 6249-6251;
9. b) X. Assfeld, J. A. Sordo, J. González, M. F. Ruiz-López, T. L. Sordo, J. Mol. Struct. (Theochem) 1993, 287, 193-199;
10. c) X. Assfeld, M. F. Ruiz-López, J. González, R. López, J. A. Sordo, T. L. Sordo, J. Commit. Chem. 1994, 15, 479-487;
11. d) R. López, T. L. Sordo, J. A. Sordo, J. González, J. Org. Chem. 1993, 58, 3263-3264;
12. e) R. López, D. Suárez, M. F. Ruiz-López, J. González, J. A. Sordo, T. L. Sordo, J. Chem. Soc. Chem. Commun. 1995, 1677-1678;
13. f) R. López, M. F. Ruiz-López, D. Rinaldi, J. A. Sordo, T. L. Sordo, J. Phys. Chem. 1996, 100, 10600-10608.
14. a) F. P. Cossío, J. M. Ugalde, X. López, B. Lecea, C. Palomo, J. Am. Chem. Soc. 1993, 115, 995-1004;
15. b) F. P. Cossío, A. Arrieta, B. Lecea, J. M. Ugalde, J. Am. Chem. Soc. 1994, 116, 2085-2093;
16. c) B. Lecea, I. Arrastia, A. Arrieta, G. Roa, X. López, M. I. Arriortua, J. M. Ugalde, F. P. Cossío, J. Org. Chem. 1996, 61, 3070-3079;
17. d) D. C. Fang, X. Y. Fu, Int. J. Quantum Chem. 1996, 57, 1107-1114.
18. M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Hill, M. W. Wong, J. B. Foresman, B. G. Johnson, B. Schlegel, M. A. Robb, 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, J. A. Pople, Gaussian 92, Revision C; Gaussian, Pittsburgh PA, 1992.
19. Adapted by D. Rinaldi from D. Rinaldi, R. R. Pappalardo, Quantum Chemistry Program Exchange, Program no. 622, Indiana University, Bloomington, IN, 1992.
20. H. B. Schlegel, J. Comput. Chem. 1982, 3, 214-218.
21. a) A. D. Becke, J. Chem. Phys. 1993, 95, 5648-5652
22. b) A. D. Becke, Phys. Rev. A. 1988, 38, 3098-3100;
23. c) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B. 1988, 57, 785-789.
24. W. J. Hehre, L. Radom, J. A. Pople, P. von R. Schleyer, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
25. D. A. McQuarrie, Statistical Mechanics, Harper & Row, New York, 1976.
26. a) J. L. Rivail, D. Rinaldi, M. F. Ruiz-López, in Theoretical and Computational Model for Organic Chemistry (NATO ASI Series C, Vol. 339) (Eds.: S. J. Formosinho, I. G. Csizmadia, L. Arnaut), Kluwer, Dordrecht, 1991, pp. 79-92;
27. b) V. Dillet, D. Rinaldi, J. G. Angyán, J. L. Rivail, Chem. Phys. Lett. 1993, 202, 18-22 ;
28. c) V. Dillet, D. Rinaldi, J. L. Rivail, J. Phys. Chem. 1994, 98, 5034-5039.
29. P. Claverie, in Quantum Theory of Chemical Reactions, Vol. 3 (Eds.: R. Daudel, A. Pullman, L. Salem, A. Veillard), Reidel, Dordrecht, 1982, pp. 151-175.
30. S. Yamabe, T. Minato, Y. Osamura, J. Chem. Soc. Chem Commun. 1993, 450-452.
31. a) K. Fukui, Acc. Chem. Res. 1981, 14, 363-375;
32. b) C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527.
33. R. López, M. I. Menéndez, D. Suárez, T. L. Sordo, J. A. Sordo, Comput. Phys. Commun. 1993, 76, 235-249.
34. W. R. Dolbier, H. Koronial, K. N. Houk, C. Sheu, Acc. Chem. Res. 1996, 29, 471-477.