— I2 9 — 



not given), was found by Til den and Shepheard at 103 (pressure 

 15 mm.). The former produced pinocampheol by reduction of pino- 

 camphone; the latter obtained it by the action of sodium nitrite on 

 pinocamphylamine hydrochloride. 



An amidocarboxylic acid derived from pinene had already been 

 obtained by Tilden and Burrows 1 ). In a further work by Tilden 

 and Blyther 2 ), the production of this acid and a number of its 

 derivates is described. Of the formulae coming under consideration: 



X.CH 3 (NH 2 ).COOH /C.CH 3 (COOH) 2 



C 6 H / and C 6 H 10 < 



\CH 2 • COOH \CH 2 .NH 2 



the former may be taken as the more probable one, but the examination 

 is continued. The acid melts at 273 with escape of carbon dioxide. 

 If pinene nitrosochloride is treated at 45 to 50 with ammonia 

 and alcohol, there is formed the well-crystallising nitrolamine 



C 7 H / I 



X C-(CH 3 ).NH 2 



which melts indistinctly at 123 to 125 , but when heated further, 

 melts again, with evolution of gas, at 129 to 13 i°, and which contains 

 approximately 1 / 2 molecule water. F. P. Leach 3 ) has produced this 

 body and identified it by various derivatives. Pinene nitrolamine 

 yields with benzaldehyde a benzylidene compound of the m. p. 162 , 

 analogous bodies with salicylic aldehyde of the m. p. 12 8°, and with 

 furfurol of the m. p. 164 . When heated with chloroform and alkalis, 

 nitrolamine gives off an odour like an isonitrile of the probable formula 



X:NOH 

 C 7 H / I 



X C(CH 3 )NC. 



Reducing agents either do not act all on pinene nitrolamine, or yield, 

 by elimination of the amido-group, Wallach's pinocamphone (oxime, 

 m. p. 86°) ±). 



Leach 5 ) further produced a pseudo-semicarbazide from 

 pinene. Potassium cyanate and pinene nitrosochloride yield in alcoholic 

 solution a compound C 12 H 17 3 N 3 having the constitution 



7 C:NO CO. 



C 7 H / )NH 

 X C(CH 3 ).NH.CCK 



*) Comp. Proceed, chem. Soc. 18 (1902), 161; Report October 1902, 

 Journ. chem. Soc. 87 (1905), 344; Report October 1905, 96. 



2 ) Journ. chem. Soc. 89 (1906), 1563. 



3 ) Proceed, chem. Soc. 22 (1906), 304; Journ. chem. Soc. 91 (1907), 1. 



4 ) Comp. Report October 1906, no. 



5 ) Proceed, chem. Soc. 22 (1906), 304; Journ. chem. Soc. 91 (1907), 10. 



9 



