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112 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

However, the explanation of the reaction, proposed by Titov and Laptev appears

to be the most probable and full. Laptev [131] and later Titov and Laptev [71]

have suggested that nitration in the presence of mercuric salts proceeds in the

following stages:

(1) Formation of a mercury-aromatic compound:

(51)

(2) Formation of a nitroso compound by the reaction of the mercury-aro-

matic compound with N 2 O 4 :

(52)

(3) Conversion of the nitroso compound into the nitro compound under the

influence of nitrogen oxides and a hydrogen ion.

The conversion may consist simply in oxidation or be the result of a more

complex reaction. For example, nitrosotoluene can be converted into diazonium

nitrate under the influence of nitrous acid. Bamberger [132] found in 1918 that

nitrosobenzene could be converted into benzenediazonium nitrate under the in-

fluence of nitrous acid. According to Bamberger [133] and Nesmeyanov [134],

mercury-aromatic compounds also give nitrates of corresponding diazonium com-

pounds under the influence of N 2 O 3 , presumably also through nitroso compounds.

(53)

Titov and Laptev also suggest the possibility of conversions with the aid of the

hydrogen ion, causing the reduction of nitroso compounds to hydroxylamine

derivatives followed by an oxidation: