- 138 - 



(m. p. 94 ; b. p. 160 [n mm. pressure]; «d in 25 per cent, ethereal 

 solution -f^O- Contrary to the dihydrofencholenic acid amide (a) 

 (m. p. 130,5°) of Mahla 1 ), Semmler designates his as (b). By 

 saponifying the amide with alcoholic potash liquor, the corresponding 

 dihydrofencholenic acid (b), (b. p. 140 to 14 1° [10 mm. pressure]; 

 ^150 0,9742; n D 1,45862; a D — J-3°i2 / ) is formed. The acid yields 

 a whole series of characteristic reaction - products. On the strength 

 of the acceptance of a dimethylated carbon-atom in fenchone next 

 to the keto-group, and of the peculiar disruption of the one 

 5 -ring in fenchone, caused by this constitutional character, Semmler 

 accepts for camphenilone an analogous disruption, provided that 

 in the latter the carbonyl - group has also next to it a dimethylated 

 carbon-atom. From camphenilone, C 9 H 14 0, there was obtained with 

 sodium amide in benzene solution, an amide which Semmler names 

 dihydrocamphoceenic acid amide (b), C 9 H 17 ON, and which has the 

 melting point 168°. By saponification, dihydrocamphoceenic acid (b), 

 C 9 H 16 2 is obtained; b. p. 138 to 13 9 (12 mm. pressure); d 2 2° 0,9815; 

 n D 1,45662. 



With regard to the constitution of fenchone and camphenilone 

 according to Semmler the two following formulae come under consid- 

 eration for the former, which illustrate the similarity between fenchone, 

 as methylcamphenilone, and camphenilone. 



H C 



H C 



I. 

 CH 



CH 9 



/CH 3 

 C< H 2 C 



\CH, 2 



CO 



II. 



CH 



CH, 



CCH 3 



fenchone 



HC 



CH 3 CH 



fenchone 





III. 



CH 



/CH 8 

 C< I^C 

 \CH 3 



/ 

 ( 



\ 

 \ 



3H 2 



CO H 2 C 



\ 



\ 



/ 

 / 



XH Q 



^CH, 



CO 



CH 



camphenilone 



Sodium amide appears to be an excellent reagent for such ring- 

 ketones, which next to the CO -group only show alkylised carbon atoms. 



Thujone. An analogous communication by A. Kotz 2 ), also 

 discussed in this Report, deals with the condensations of cyclopentanone, 

 isothujone, and thujone, with oxalic ester. The production of 

 cyclopentanone- 2 -oxalic acid ester- 1, 



*) With regard to Kondakow's view of the correctness of Semmler's fenchone 

 formula, see p. 118. 



2 ) Liebig's Annalen 348 (1906), in; comp. also the present Report p. 148. 



