[Synthesis and Reactivity of Ynhydrazines]

Decroutte, H.;Janousek, Z.;Pongo, L.;Merenyi, R.;Viehe, HG.
(1990) Societe Chimique de France. Bulletin — n° 6, p. 745-750 (1990)

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  • Decroutte, H.
    Author
  • Janousek, Z.
    Author
  • Pongo, L.
    Author
  • Merenyi, R.
    Author
  • Viehe, HG.
    Author
Abstract
The first examples of ynhydrazines are described of which the 1-trimethylhydrazino-2-phenylacetylene 4 is studied in particular. Besides the expected reactivity, analogous but weaker than that of the corresponding ynamine towards phenol, cyanhydric acid, allylic alcool, benzoic anhydride, benzaldehyde and formaldehyde, this ynhydrazine undergoes smooth retro-ene type fragmentation producing N-methyl-phenylketenimine above 100-degrees-C. Another particularity is heterocyclization with phosgene producing a pyrazolone derivative through dechloromethylation.
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Decroutte, H., Janousek, Z., Pongo, L., Merenyi, R., & Viehe, HG. (1990). [Synthesis and Reactivity of Ynhydrazines]. Societe Chimique de France. Bulletin, 6, 745-750. https://hdl.handle.net/2078.5/67086 (Original work published 1990)