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NC(=O)c1nonc1O

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"Constitution of the Fulminuric Acids. VII. Isofulminuric Acid" Gazzetta Chimica Italiana V 42, Is I, P 503-17, Journal 1912 CODEN:GCITA9 ISSN:0016-5603

By: Ulpiani, C.
cf. C. A., 6, 2236.  The salt obtained by Nef in the hydrolysis of HON : C(CN)​C( : NOH)​OH (Ann., 280, 291) is not K hydroxy-​furazanecarboxylate (I) but potassium isonitrosomalonhydroxamate, HON : C(OH)​- C( : NOH)​CO2K. However, although his reasoning was based on incorrect grounds, his view that the compds. obtained by Ehrenberg by the action of HCl on dry Hg fulminate in Et2O and subsequent treatment with NH3 (J. Prakt. Chem., 30, 38) are derivs. of hydroxyfurazanecarboxylic acid is correct.  The supposed amidine, however, which does not m. up to 315° and gives a violet cryst. ppt. with NH3-​CuSO4, does not give a blood-​red color with FeCl3, contrary to N.'s statement.  When b. with Ba(OH)​2, it loses NH3 and gives hydroxyfurazanecarboxylic acid; instead of a hydroxy amidine, it is an amino amide (II)​.  Again, E.'s supposed α-​isofulminuric acid is not infusible and does not give a red color with FeCl3, but is identical with Scholvien's β-​isofulminuric acid (J. prakt. Chem., 33, 461)​, m. 204-​5°.  With Ba(OH)​2, it gives hydroxyfurazanecarboxylic acid.  It is the corresponding amide (III)​, for when the ethyl ester of the furazane acid, from the acid in alc. and HCl, crystals with 1 H2O, m. 45°, is treated with NH3, it gives the ammonium salt of the ester, needles, m. 185-​6° (decomp.)​, which, when satd. in alc. with dry NH3, yields the ammonium salt of the amide, needles, m. 200-​2°, and this, with HCl, forms a compd. identical with S.'s acid. 

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