174 



volatilises with difficulty with steam, but no camphene is produced. It 

 is only when the temperature of the reaction is raised to the boiling 

 point of aniline that a very copious formation of camphene takes place. 

 The reaction may be carried out in open vessels; the camphene must be 

 driven over by direct distillation, for steam distillation only yields from 

 30 to 40°/o camphene, together with from 30 to 45% bornyl aniline. The 

 following is the explanation of this remarkable phenomenon: The reaction 

 of bornyl chloride with aniline gives rise in the first place to bornyl 

 aniline, which under the influence of the aniline hydrochloride, at the 

 high temperature which is only reached by direct distillation, gives off 

 aniline, camphene being formed: — 



H 2 C 

 H 2 C 



+ 2C 6 H 6 NH 2 = 



CHC1 



C-CH 3 



Bornylchloride 



+ C 6 H 6 NH 2( HC1 — 



H 2 C 



H*C 



CCH 3 



Bornylaniline 



CCH 3 



Camphene 



Similar reactions are given by the toluidines and by xylidine. The 

 authors describe a series of bornylarylamines with their derivatives, of 

 which a summary may here be given: — 



Bornylaniline, Ci Hi 7 NH • C 6 H 5 , is formed in the course of 3 hours' 

 boiling of 7 parts bornylchloride with 15 parts aniline. It occurs as a 

 colourless liquid, highly refractive of light, insoluble in water, but soluble 

 in alcohol, ether, benzene and glacial acetic acid: b. p. 140° (2 mm), m. p. 

 of the hydrochloride 198°. Bornylacetanilide, CioH 17 N(COCH 3 )C 6 H 5 , is 

 produced by heating bornyl aniline with acetic anhydride and anhydrous 

 acetate of soda in a reflux condenser; it crystallises out from light petro- 

 leum in prisms, m. p. 123°. Bornylaceto-p-nitraniline, Ci Hi 7 N(COCH 3 ) 

 • C 6 H 4 • N0 2 is produced by nitrating bornylacetanilide ; it forms white leaflets, 

 m.p. 158°. When reduced it yields bornyl acetophenylenediamine (m.p. 148°). 

 Bornyl-o-toluidine, CioHi 7 NHC 6 H 4 • CH 3 occurs as a liquid, b. p. 160° 

 (4 mm), which soon congeals into needles melting at 55°. The hydro- 



