Journal of Organic Chemistry p. 2252 - 2257 (1992)
Update date:2022-08-03
Topics:
Hadjiantoniou-Maroulis, C. P.
Maroulis, A. J.
Terzis, A.
Mentzafos, D.
The synthesis and the Pb(OAc)4 oxidation of the mixed bishydrazones of biacetyl 7 was studied.The formation of the novel N-benzoyl-1,2,3-triazol-1-imines 9 from the oxidation of 7 provided support to the proposed in the past mechanism for the oxidation of bis-aroylhydrazones of α-dicarbonyl compounds 4.Thermolysis and photolysis of 9a in DMSO was carried out.The results suggested that benzoylnitrene was formed in the photochemical reaction, and therefore compounds such as 9 could serve as non-azide aroyl nitrene precursors.For 9a the results of the X-ray analysis were correlated with charge densities and bond orders gleaned by the MNDO method.Product 9d was alternatively synthesized by the addition of photochemically generated bezoylnitrene to the 1,2,3-triazole 21.
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