— 196 — 



carvone hydrazine compound affords A 8 9 -menthene (b. p. 170°). With 

 fuming hydrobromic acid, J 8,9 -menthene yields a bromide which, upon 

 being boiled with aniline, affords zJ 4,8 -menthene (b. p. 170,5 to 172,5°), and 

 with 20°/o sulphuric acid, zl 3 -menthene. The carvenone hydrazine com- 

 pound, when heated with solid potassium hydroxide, yields zl 3 -menthene. 

 The citronellal hydrazine compound yields a hydrocarbon CioHi 8 , b. p. 164,5°. 

 The hydrazine compound of citral gives rise to a hydrocarbon Ci Hi 8 (b. p. 

 164 to 165°). 



v. Baeyer assumes that the relation of bisnitrosyl carone towards 

 carone bisnitrosylic acid, which is obtained by treating the first-named 

 body with hydrochloric or sulphuric acid, corresponds to the relation of 

 ether to alcohol. Bamberger 1 ), however, takes another view of the con- 

 version. He argues from the known fact that all the C-nitroso bodies are 

 capable of forming monomolecular solutions, and that the bimolecular 

 forms are less energetic than the monomolecular forms. The last-named 

 he regards as the reactions of all (7-nitroso compounds, including the 

 bisnitrositised. In his opinion the conversion of bisnitrosylcarone yields 

 first monomolecular hitrosyl carone, which latter is split up by the action 

 of hydrogen chloride into chlorocarone and Angeli's nitroxyle. The latter, 

 with a second molecule of nitrosocarone, affords carone bisnitrosylic acid 

 (carone nitrosohydroxylamine, the conversion proceeding as follows: — 



C 10 H 15 O-NO + HCl =C 10 H 15 O-Cl + NOH 

 doHrsONO + NOH-doHxsON^-OH 



X NO' 



Bamberger's views are based upon observations made by him in 

 v. Baeyer's own researches on the conversions: bisnitrosyl menthone — > 

 menthone-bisnitrosylic acid and chloromenthone, and bisnitroso pule- 

 gone — >■ pulegone-bisnitrosylic acid and chloropulegone. The change 

 in colour which is observed when a solution of isosafrol- or anethol 

 pseudonitrosite is alternately warmed and cooled down in glacial acetic 

 acid, benzene or chloroform, is attributed by Bamberger to a manifestation 

 of desmotropy, but he does not oppose the view that, in the main, a 

 decomposition of a different kind takes place when the solutions are warmed. 



Dihydrocarvylamine. According to G. F. Morrell 2 ), when an 

 ethereal solution of dihydrocarvylamine is saturated with hydrochloric 

 acid gas, the result is a chlorinated base, chlorotetrahydrocarvylaminf 

 (m. p. 205°), which, when heated with pyridine, yields a mixture of a- and 

 /?-dihydroterpenylamine. Both bodies are difficult to obtain in the pure 



• 



!) Bed. Berichte 44 (1911), 3066. 

 2 ) Berl. Berichte 44 (1911), 2560. 



