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NITRO DERIVATIVES OF TOLUENE 301

perature (-10°C), he found that one molecule of trinitrotoluene absorbs two of
ammonia to form a complex to which the author ascribed the following formula:

(cf. Faar, Bard and Wheland [160]).

Hantzsch and Kissel [81] by treating trinitrotoluene with potassium alcoholate
(e.g. methylate) obtained an addition product to which they ascribed the structure

given earlier by Angeli [82] for the product obtained from trinitrobenzene and

CH 3 OK (I).

I

In accordance with Meisenheimer’s work [83, 84] (p. 202), however, the

structure should be presented by the formula II (using the more modem annotation).

Further studies (Hantzsch and Picton [85]) showed, that inorganic acids, e.g.

sulphuric, decompose these salts, with the evolution of nitrogen oxides. Products

of a drastic transformation of trinitrotoluene are precipitated simultaneously,

among them stilbene derivatives, products of oxidation of the methyl group.

Copisarow [86] tried to express the changes which trinitrotoluene undergoes

under the action of alcoholates or alkali metal hydroxides by the following scheme,

in which he postulated the formation of nitro-nitroso derivatives of dibenzyl (III),

and stilbene (IV), followed by the formation of an azoxy compound (V), which

might be transformed into more complex azoxy compounds: