Rearrangement of substituted azido-1,2,3-triazolides to (α-diazoalkyl)-tetrazolides

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 1998, Pages 785-790

  Preu, Lutz ^a   Beißner, Andreas ^a   Moderhack, Dietrich ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0348228003     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708872h     Document Type: Article

References (30)

1. Overviews: J. Elguero, R. M. Claramunt and A. J. H. Summers, Adv. Heterocycl. Chem., 1978, 22, 183;
2. Overviews: J. Elguero, R. M. Claramunt and A. J. H. Summers, Adv. Heterocycl. Chem., 1978, 22, 183; D. Moderhack, in Comprehensive Heterocyclic Chemistry II, eds. A. R. Katritzky C W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 8 (ed. G. Jones), p. 227
3. R. M. Claramunt, J. Elguero, A. Fruchier and M. J. Nye, Afinidad, 1977, 34, 545.
4. D. Moderhack and L. Preu, J. Chem. Soc., Chem. Commun., 1988, 1144.
5. J. A. C. Gorini, J. Farràs, M. Feliz, S. Olivella, A. Solé and J. Vilarrasa, J. Chem. Soc., Chem. Commun., 1986, 959.
6. See also: (a) D. Moderhack and A. Beißner, J. Prakt. Chem./Chem.-Ztg. 1997, 339, 582;
7. (b) N. C. Mathur and H. Shechter, J. Org. Chem., 1990, 55, 3001.
8. R. S. Klein, F. G. De Las Heras, S. Y.-K. Tam, I. Wempen and J. J. Fox, J. Heterocycl. Chem., 1976, 13, 589.
9. (a) D. R. Sutherland and G. Tennant, J. Chem.Soc. C, 1971, 2156;
10. (b) C. Mayor and C. Wentrup, J. Am. Chem. Soc., 1975, 97, 7467;
11. (c) cf. E. Lieber, C. N. R. Rao and T. V. Rajkumar, J. Org. Chem., 1959, 24, 134.
12. A. Albert, J. Chem. Soc. C, 1968, 2076.
13. D. Stadler, W. Anschütz, M. Regitz, G. Keller, D. Van Assche and J.-P. Fleury, Liebigs Ann. Chem., 1975, 2159.
14. M. F. Gordeev, A. V. Komkov, V. S. Bogdanov and V. A. Dorokhov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1392; Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 29, 1256.
15. M. F. Gordeev, A. V. Komkov, V. S. Bogdanov and V. A. Dorokhov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1392; Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 29, 1256.
16. R. Mertz, D. Van Assche, J.-P. Fleury and M. Regitz, Bull. Soc. Chim Fr., 1973, 3442.
17. H. Behringer and K. Kohl, Chem. Ber., 1956, 89, 2648.
18. D. Moderhack and A. Beißner, Z. Naturforsch., Teil B, 1996, 51, 1815.
19. D. Moderhack and K.-H. Goos, Chem. Ber., 1987, 120, 921.
20. S. Oae and Y. Uchida, in The Chemistry of Sulphones and Sulphoxides, eds. S. Patai, Z. Rappoport and C. Stirling, Wiley-Interscience, Chichester, 1988, p. 583.
21. M. Regitz and G. Maas, Diazo Compounds - Properties and Synthesis, Academic Press, Orlando, 1986, p. 368.
22. M. Rull and J. Vilarrasa, Tetrahedron Lett., 1976, 4175.
23. E. Alcalde, J. de Mendoza and J. Elguero, J. Chem. Soc., Chem. Commun., 1974, 411; J. Heterocycl. Chem., 1974, 11, 921.
24. E. Alcalde, J. de Mendoza and J. Elguero, J. Chem. Soc., Chem. Commun., 1974, 411; J. Heterocycl. Chem., 1974, 11, 921.
25. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209.
26. S. Olivella and J. Vilarrasa, J. Heterocycl. Chem., 1979, 16, 685.
27. G. Heublein, P. Hallpap, S. Hauptmann and G. Mann, Einführung in die Reaktionstheorie, VEB Deutscher Verlag für Grundstoff-industrie, Leipzig, 1984, p. 98.
28. G. I. Gellene, J. Chem. Educ., 1995, 72, 196.
29. G. L'abbé and L. Beenaerts, Bull. Soc Chim. Belg., 1989, 98, 421.
30. MOPAC version 7.0 (public domain programme for PC), ftp:// infomeister.osc.edu/pub/chemistry/software/MS-DOS/.