C. Palazzo (1907) support this formula, finding that methyl nitrolic acid, NO 2 CH: N-OH, yielded under certain conditions fulminic acid, and vice versa (Palazzo, 1907).
Closely related to the amidoximes are the nitrolic acids, R C(NO 2): NOH.
The proof of this was left for Hantzsch, who traced a connexion with the nitrolic acids of V.
The primary compounds form nitrolic acids of the type R C (: NOH) NO, the secondary yield pseudo-nitrols of the type RR': C(NO)(NO 2), whilst the tertiary nitro compounds are not acted upon by nitrous acid.
The nitrolic acids, R.
When heated with water and mineral acids, the nitrolic acids are completely decomposed, yielding fatty acids and nitrous oxide.
1898, 31, p. 2854) described several series of salts of the nitrolic acids, with particular reference to ethylnitrolic acid.
They discriminate between the red or erythro-salts, which are well crystallized, very explosive and unstable compounds, and which regenerate the colourless nitrolic acid on the addition of dilute mineral acids, and the leuco-salts, which are colourless salts obtained by warming the erythro-salts or by exposing them to direct sunlight.
The following structural formulae are assigned to these compounds: R CAN OH R.CCN(OK) > O R C N02K NO 2 N(:O) NO nitrolic acid; erythro-salt; leuco-salt.
By this treatment a primary nitro-alkyl yields a nitrolic acid, the potassium salt of which forms an intense red solution; a secondary nitro-alkyl forms a pseudo nitrol, which gives an intense blue solution, while the tertiary compound does not act with nitrous acid.