180 Proceedings of the Royal Irish Academy. 



Pfeiffer and Monath i Her. d. Dtsch. Chem. Ges. xxxix (1906), pp. 1304- 

 1306) have shown that o -trinitrotoluene reacts readily with benzaldehyde 

 in the presence of piperidine, yielding 2.4.6-trinitrostilbene. 



Pfeitt'er (Ber. d. Dtsch. Uhein. ties \lviii (1915), p. 1777) has prepared 

 further stilbene derivatives by the same reaction. 



IV. Action of Hydrocarbons. 



Hepp (Liebig's Annalen der Chemie, ccxv, pp. 375-380) showed that 

 s-trinitrobenzene and a-, /3-, and y-trinitrotoluene combine with aromatic 

 hydrocarbons such as benzene, naphthalene, and anthracene. Sudborough 

 (Jonrn. Chem. 8oc. L916, pp. 1339-1348) lias further examined the behaviour 



-trinitrobenzene in this respect, and has announced his intention of 

 studying these additivi tnpounds Bpectroscopically. 



B. — EXPERIMENTAL PART. 



I. Action of Aqueous Alkalies on s-Trinitrobenzene. 



Five grams of i-trinitrobenzene were heated on the water-bath with 

 50 cc. of 5 p. c caustic soda. < >n heating the liquid an orange-red colour 

 developed, which then became brown, and finally dark brown, ammonia being 

 evolved during the reaction. After half an hour the dark-coloured solid was 

 separated, washed well, and dried. It was then extracted with benzene, in 

 which the main portion dissolved, leaving a dark, almost black, insoluble 

 residue which exploded when heated. The benzene solution on concentra- 

 tion yielded a yellowish solid, melting at 175-180 C, and which on recrys 



tallisation from alcohol-acetone melted al 185 C, and ga*i analysis the 



following results : — 



0*1242 grams si gave 24*2 cc. moist nitrogen al 16 C 



and 75 1 m.m.p. 



( "i responding tn N i'L'."..". 



0„1J V requires X 2222. 



Hence the substance is probably Utranitro-azoxyhenzene. It is soluble in 

 benzene and acetone, and slightly soluble in alcohol. In acetone Bolution it 



- with • 1 a a violet clour, which is decolourised by hydro- 



chloric acid. The tetranitro-azoxytoluene ol Anschiitz and Zinimennann 

 milar coloration with caustic soda. 



The mother-liquors gave a solid melting al 200 220 ' '.. bul the 



amount of il mall for furthei examination. 



