Depending on the substitution on the hydrazine moiety, thermolysis of 3-phenyl-1,2,4-oxadiazol-5-ylhydrazines (1)-(5) gives variable amounts of 1-amino-Δ2-1,2,4-triazolin-5-ones (13) or (17), Δ2- or Δ3-1,2,4-triazolin-5-ones (12), (18), or (19), and the s-triazine (20). A possible mechanism accounting for the products and the effects is discussed. A diradical intermediate and a hydrogen transfer from the reaction medium are suggested on the basis of the effect of benzoyl peroxide on the reaction and on the behaviour of the hydrazines (1)-(4) towards catalytic hydrogenation.
Adembri, G., Camparini, A., Ponticelli, F., Tedeschi, P. (1981). Thermal Behaviour of 3-Phenyl-1,2,4-oxadiazol-5-ylhydrazines. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I, 1703-1706 [10.1039/P19810001703].
Thermal Behaviour of 3-Phenyl-1,2,4-oxadiazol-5-ylhydrazines
Adembri, Giorgio;Camparini, Alfredo;Ponticelli, Fabio;
1981-01-01
Abstract
Depending on the substitution on the hydrazine moiety, thermolysis of 3-phenyl-1,2,4-oxadiazol-5-ylhydrazines (1)-(5) gives variable amounts of 1-amino-Δ2-1,2,4-triazolin-5-ones (13) or (17), Δ2- or Δ3-1,2,4-triazolin-5-ones (12), (18), or (19), and the s-triazine (20). A possible mechanism accounting for the products and the effects is discussed. A diradical intermediate and a hydrogen transfer from the reaction medium are suggested on the basis of the effect of benzoyl peroxide on the reaction and on the behaviour of the hydrazines (1)-(4) towards catalytic hydrogenation.
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https://hdl.handle.net/11365/6820
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