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

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

  • Organische Chemie und Biochemie
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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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Authors and Affiliations

  1. Institut für Organische und Pharmazeutische Chemie der Universität Innsbruck, Innrain 52a, A-6020, Innsbruck, Österreich

    J. Schantl

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  1. J. Schantl
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Oxidationsprodukte von Arylhydrazon-Verbindungen, 9. Mitt. (8. Mitt.1).

1J. Schantl, Mh. Chem.105, 220 (1974).

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Schantl, J. 3,6-Dialkyl-1-phenyl-6-phenylazo-1,4,5,6-tetrahydropyridazine, (4+2)-Cycloadditionsprodukte aus 2-Phenylazo-1-alkenen, 2. Teil: Reaktionen. Monatshefte für Chemie 105, 229–239 (1974). https://doi.org/10.1007/BF00911311

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