The oxidation of dithizone [3-mercapto-1,5-diphenylformazan, C13H12N4S, (I); R = SH] under alkaline conditions to a sydnone, C13H10N4S (II), is reversible; however under acid conditions elimination of a proton from the ortho-position of one of the phenyl residues leads to a purple isomer with a new bicyclic ring system (IV), the structure of which has been established by X-ray structure analysis.
W. S. McDonald, H. M. N. H. Irving, G. Raper and D. C. Rupainwar, J. Chem. Soc. D, 1969, 392b DOI: 10.1039/C2969000392B
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