Theoretical study of pericyclic reactions of nitrosoethylene and (thionitroso)ethylene

Liebigs Annales

Volumn , Issue 10, 1996, Pages 1615-1621

  Sperling, Dirk ^a   Mehlhorn, Achim ^a   Reißig, Hans Ulrich ^a   Fabian, Jürgen ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Calculations, ab initio, semiempirical; Electrocyclic reactions; Hetero Diels Alder reaction; N,O Heterocycles; N,S Heterocycles; Nitroso compounds; Thionitroso compounds; Transition structures

Indexed keywords

EID: 33749082301     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619961018     Document Type: Article

References (35)

1. K. N. Houk, J. Gonzales, Y. Li, Acc. Chem. Res. 1995, 28, 81.
2. [2a] D. L. Boger, S. N. Weinreb in Hetero-Diels-Alder Methodology in Organic Synthesis (Ed.: H. H. Wasserman), Academic Press Inc., San Diego, 1987.
3. [2b] W. Carrathers in Cycloaddition Reactions in Organic Synthesis (Eds.: J. E. Baldwin, P. D. Magnus), Pergamon Press, Oxford, 1990.
4. [2c] J. Jurczak, T. Bauer, C. Chapuis in Methoden Org. Chem. (Hauben- Weyl) 4th Ed. 1995, vol. E 21c, p. 2905-2952.
5. J.-M. Surzur, C. Dupuy, M. P. Bertrand, R. Nouguier, J. Org. Chem. 1972, 37, 2782.
6. [4a] T. L. Gilchrist, Chem. Soc. Rev. 1983, 12, 53.
7. [4b] C. Hippeli, H.-U. Reißig, Llebigs Ann. Chem. 1990, 217.
8. [4c] C. Hippeli, H.-U. Reißig, T. Arnold, Chem. Ber. 1990, 123, 2403.
9. [4d] R. Zimmer, H.-U. Reißig, Liebigs Ann. Chem. 1991, 553.
10. J. M. Ugalde, J. Mol. Struct. 1992, 258, 167.
11. B. S. Jursic, Z. Zdravkovski, J. Org. Chem. 1995, 60, 3163.
12. K. N. Houk, private communication to one of the authors (H.-U. R.).
13. D. Sperling, J. Fabian, Sulfur Lett. 1996, 19, 189.
14. [9a] L. N. Markovsky, V. V. Penkovsky, Yu. G. Shermolovich, Rev. Heteroat. Chem., 1993, 9, 21.
15. [9b] M. Takahashi and R. Okazaki, Sulfur Rep. 1993, 13, 293.
16. E. Breuer in Nitrones, Nitronates and Nitroxides (Eds.: S. Patai, Z. Rappoport), J. Wiley, New York, 1989, p. 139-312.
17. R. Grashey in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), J. Wiley, New York, 1984, part 1, p. 733.
18. J. J. P. Stewart, J. Comp. Chem. 1989, 10, 209.
19. SPARTAN Electronic Structure Program, Wavefunction Inc., 18401 Von Karman Avenue, Suite 370, Irvine, California, 92715 USA.
20. Gaussian 92, Revision B, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. 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, Inc., Pittsburgh, PA, USA, 1992.
21. Gaussian 94, Revision B. 2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. 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 J. A. Pople, Gaussian, Inc., Pittsburgh PA, USA, 1995.
22. W. J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab initio Molecular Orbital Theory, J. Wiley, New York, 1986.
23. R. J. Bartlett, J. F. Stanton in Reviews in Computational Chemistry (Eds.: K. B. Lipkowitz, D. B. Boyd), VCH Publ., New York, 1994, vol. 5, p. 65.
24. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
25. M. W. Wong, M. J. Frisch, K. B. Wiberg, J. Am. Chem. Soc. 1991, 113, 4776.
26. K. B. Wiberg, P. R. Rablen, M. Marquez, J. Am. Chem. Soc. 1992, 114, 8654.
27. K. Wieser, A. Berndt, Angew. Chem. 1975, 87, 73;
28. Angew. Chem. Int. Ed. Engl. 1975, 14, 70.
29. K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711;
30. Angew. Chem. Int. Ed. Engl. 1992, 31, 682.
31. I. Fleming, Grenzorbitate und Reaktionen organischer Verbindungen, VCH, Weinheim, 1990.
32. K. N. Houk, J. Am. Chem. Soc. 1973, 95, 4092, and papers quoted therein.
33. See for instance: [25a] J. J. W. McDouall, M. A. Robb, U. Niazi, F. Bernardi, H. B. Schlegel, J. Am. Chem. Soc. 1987, 109, 4642.
34. [25b] F. Bernardi, A. Bottoni, M. J. Field, M. F. Guest, I. H. Hillier, M. A. Robb, A. Venturini, J. Am. Chem. Soc. 1988, 110, 3050.
35. K. B. Wiberg, P. R. Rablen, J. Comput. Chem. 1993, 14, 1504, and papers quoted therein.