— 185 — 



phorone) 1 ). The formation of this ketone is readily accounted for by the 

 presence in the original hydrocarbon-mixture of z1 1 -methyl-l-{sopropyl-3- 

 c*/cZopentene. 



Wallach further describes some new derivatives of fencholic acid. 

 The nitrile of the acid (IV) is formed by the conversion of the amide of 

 fencholic acid with phosphorus pentoxide: b. p. 217 to 218°, d 19o 0,8660, 

 n D19Q 1,4433. The nitrile obtained from d-fenchone rotates +5° 45'. The 

 reaction of the fencholic acid nitrile with metallic sodium yields methyl- 

 tsopropylci/dopentyl methylamine: b. p. 204°, d 20O 0,8500, n D20O 1,4545, m. p. 

 of the hydrochloride 172 to 173°. The conversion of the base with nitrous 

 acid was of special interest because in this reaction, according to the 

 experience obtained with cydopentyl methylamine a widening of the ring 

 was to be expected. As a matter of fact the substituted methylamine 

 formed a menthanol, perhaps consisting of a mixture of p- and m-menthanol-1 . 

 Hence a hexa-ring had been formed. In addition to the alcohols, the base 

 yielded a hydrocarbon Ci Hi 8 , possessing the properties of carvomenthene. 



The reaction of nitrous acid with fenchelylamine 2 ) (amido-1 -methyl- 1- 

 ?sopropyl-3-c?/dopentane) yielded a ring-homologue of p-menthanol-1 (hydrated 

 ^-terpineol), namely methyl- l-isopropyl-3-ci/cZopentanol-l (V). 



The paper also refers to certain compounds of fenchonitrile. The 

 nitrosochloride of a-fenchonitrile melts at 123 to 124° and is strongly 

 laevoratatory. «-Fenchonitrile reconstituted from the nitrosochloride gives 

 diso 0,749, [«] D + 43,19° (in 14,56% ethereal solution). 



The fenchonitriles of different origin, when oxidised with 1 °/o solution 

 of permanganate of potassium at 0° yielded similar products. Oxidation 

 gave rise to dihydroxydihydrofenchonitrile (m. p. 86°); the corresponding 

 acid, dihydroxydihydrofencholenic acid, melting at 1 1 1°. As the relationship 

 between the known hydrated fencholenic acids and a- and /^-fencholenic 

 acid is as yet unknown, the latter were reduced by Paal's method 3 ). It 

 was then found that the product of reduction of /^-fencholenic acid (VI) 

 is identical with fencholic acid 4 ). The product of reduction of a-fencholenic 

 acid is probably identical with dihydro fencholenic acid, which has been 

 prepared from fenchimine by Mania 5 ). 



CCH 3 CCH 3 CHCH 3 



Hc/\cu 2 H 2 C^CH H 2 c/\cO 



! ! 

 CHC3H7 H 2 C — — CHC3H7 



I. J 5 -methyI-l-isopropyI- II. J 1 -methyI-l-/5opropyl- III. dihydropulegenone 



3- cy clop entene. 3-ci/c?opentene. (dihydrocamphorphorone). 



H 2 C J CH-CsH? H 2 C 



J ) Comp. Report October 1903, 91. 



2 ) Comp. Report April 1910, 183. 



3 ) Comp. p. 164. 



4 ) Comp. Report April 1910, 181. 



■'•) Berl. Berichte 34 (1901), 3779; Report April 1902, 92. 



