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-, (4+2)-cycloaddition products from 2-phenylazo-1-alkenes. Part 2: Reactions


Catalytic hydrogenation of 3.6-dialkyl-1-phenyl-6-phenylazo- 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 monophenylhydrazone (10) which undergoes ready oxidation to 3.6-di-t-butyl-6-phenylazo-1.2-dioxan-3-ol (12).


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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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