Monatshefte für Chemie / Chemical Monthly

, Volume 105, Issue 1, pp 229–239 | Cite as

3,6-Dialkyl-1-phenyl-6-phenylazo-1,4,5,6-tetrahydropyridazine, (4+2)-Cycloadditionsprodukte aus 2-Phenylazo-1-alkenen, 2. Teil: Reaktionen

  • J. Schantl
Organische Chemie und Biochemie

3.6-Dialkyl-1-phenyl-6-phenylazo-1.4.5.6-tetrahydropyridazines, (4+2)-cycloaddition products from 2-phenylazo-1-alkenes. Part 2: Reactions

Abstract

Catalytic hydrogenation of 3.6-dialkyl-1-phenyl-6-phenylazo-1.4.5.6-tetrahydropyridazines2 a-e gives crystalline bisphenylhydrazones of 1.4-diketones4 a-e; in solution,4 exists as a mixture of geometrical isomers due to the two phenylhydrazone functions. Reaction of2 a-f with H2NOH yields the dioximes of 1.4-diketones5 a-f. On acid hydrolysis of2, the 6-phenylazo substituent undergoes some reactions and yields products typical of the intermediate “zwitterionic” phenyldiazene. Thus, the tetrahydropyridazine part of2 d yields 1-anilino-2.5-diisopropyl-pyrrole (9), that of2 e gives 2.2.7.7-tetramethyl-3.6-octanedione monophenylhydrazone (10) which undergoes ready oxidation to 3.6-di-t-butyl-6-phenylazo-1.2-dioxan-3-ol (12).

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Literatur

  1. 2.
    G. J. Karabatsos, R. A. Taller undF. M. Vane, J. Amer. Chem. Soc.85, 2326 (1963);G. J. Karabatsos undR. A. Taller, J. Amer. Chem. Soc.85, 3624 (1963).Google Scholar
  2. 3.
    E. Lustig, J. Phys. Chem.65, 491 (1961).Google Scholar
  3. 4.
    C. Paal, Ber. dtsch. chem. Ges.18, 58 (1885).Google Scholar
  4. 5a).
    K. Heß undF. Wissing, Ber. dtsch. chem. Ges.47, 1416 (1914);Google Scholar
  5. 5b).
    E. E. Blaise, C. r. hebdomad. Sé. Acad. Sci.158, 1686 (1914).Google Scholar
  6. 6.
    K. Bowden, I. M. Heilbron, E. R. H. Jones undB. C. L. Weedon, J. Chem. Soc.1946, 39.Google Scholar
  7. 7a).
    A. Spassoff, Bull. Soc. Chim. [5],4, 1658 (1937),Google Scholar
  8. 7b).
    L. F. Deemer, L. Lutwak undF. M. Strong, J. Amer. Chem. Soc.70, 154 (1948).Google Scholar
  9. 8.
    E. Wahlberg, Ber. dtsch. chem. Ges.65, 1857 (1932).Google Scholar
  10. 9.
    J. Schantl, Mh. Chem.101, 1339 (1970).Google Scholar
  11. 10.
    A. J. Bellamy undR. D. Guthrie, J. Chem. Soc.1965, 2788.Google Scholar
  12. 11.
    J. Schantl, Mh. Chem. (im Druck).Google Scholar
  13. 12a).
    C. Liebermann, Ber. dtsch. chem. Ges.7, 247, 806, 1098 (1874);Google Scholar
  14. 12b).
    F. Feigl undV. Anger, Spot Tests in Organic Analysis, S. 290. Amsterdam: Elsevier, 1966.Google Scholar
  15. 13.
    Ref., S. 300..Google Scholar
  16. 14.
    M. S. Kharasch, H. C. McBay undW. H. Urry, J. Amer. Chem. Soc.70, 1269 (1948).Google Scholar

Copyright information

© Springer-Verlag 1974

Authors and Affiliations

  • J. Schantl
    • 1
  1. 1.Institut für Organische und Pharmazeutische Chemie der Universität InnsbruckInnsbruckÖsterreich

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