On the Preparation of 5-(α-Diazoethyl)tetrazoles

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 51, Issue 12, 1996, Pages 1815-1817

  Moderhack, Dietrich ^a   Beißner, Andreas ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

5 ( Diazoethyl)tetrazoles; Dehydrogenation; Methyl Tetrazol 5 yl Ketone Hydrazones; Silver(I) Oxide

Indexed keywords

KETONES; SILVER OXIDES; SODIUM HYDROXIDE;

HYDRAZONES; SILVERS (I); TETRAZOLES; TITLE COMPOUNDS;

DEHYDROGENATION;

EID: 0347246382     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-1996-1220     Document Type: Article

References (24)

1. Ring transformations of the principle: D. Moderhack, L. Preu, J. Chem.Soc., Chem.Commun. 1988, 1144.
2. a) M. Regitz, G. Maas, Diazo Compounds - Properties and Synthesis, Academic Press, New York (1986);
3. b) M. Böhshar, J. Fink, H. Heydt, O. Wagner, M. Regitz, Diazo-Verbindungen, in: D. Klamann, H. Hagemann, Methoden der organischen Chemie (Houben-Weyl), 4th ed., Vol. E 14b, Part 2, Thieme, Stuttgart (1990):
4. c) H. Zollinger, Diazo Chemistry II - Aliphatic, Inorganic and Organometallic Compounds, VCH, Weinheim (1995).
5. a) A. Andrus, J. V. Heck, B. G. Christensen, B. Partridge, J. Am. Chem. Soc. 106, 1808 (1984);
6. b) G. L'abbé, M. Gelinne, S. Toppet, J. Heterocycl. Chem. 25, 1741 (1988) [in our hands, the compound 6a described therein did not form under the conditions reported (in contrast to its isomer 5a)].
7. D. Moderhack, K.-H. Goos, Chem.Ber. 120, 921 (1987).
8. K.-H. Goos, Dissertation, Technische Universität Braunschweig (1985).
9. a) E. K. Harvill, R. M. Herbst, E. G. Schreiner, J. Org. Chem. 17, 1597 (1952);
10. b) C. R. Jacobson, A. B. Kerr (Jr.), E. D. Amstutz, J. Org. Chem. 19, 1909 (1954);
11. c) C. R. Jacobson, E. D. Amstutz, J. Org. Chem. 19, 1652 (1954);
12. d) B. E. Fisher, A. J. Tomson, J. P. Horwitz, J. Org. Chem. 24, 1650 (1959).
13. D. Moderhack, A. Lembcke, Chem.-Ztg. 108, 188 (1984).
14. O. Gryszkiewicz-Trochimowski, C. R. Acad.Sci. 246, 2627 (1958).
15. R. J. Spear, Aust. J. Chem. 37, 2453 (1984).
16. D. Moderhack, A. Beißner, Z. Naturforsch. 47b, 1803 (1992).
17. For a different reactivity of stereoisomers in the Bamford-Stevens reaction, see ref.[4] and the literature cited therein.
18. In the case of 2 → 4, some deacetylation was observed as side reaction (formation of 1-methyltetrazole and acetohydrazide); for this behaviour cf. ref.[6c] and D. Moderhack, Liebigs Ann.Chem. 758, 29 (1972).
19. This reaction cannot be exploited preparatively, because sensitivity of 5 towards chromatographic adsorbents vitiates separation of the isomers (see also the instability of 2-substituted 5-(diazomethyl)tetrazoles [5]).
20. 3.
21. Cf. ref.[2c], p. 16.
22. 1H NMR only).
23. 3): δ = 2.11 (d, J = 8 Hz, 3 H, CHMe), 4.17 (s, 3 H, NMe), 5.30 (q, J = 8 Hz, 1 H, CHMe).
24. Ref.[8] reports m.p. 173-175 °C (identity of compound however questionable in view of impure precursor to 5).