108 Report of Schimmel § Co. 1921. 



and isopropylbenzylketone yield reaction products with this ester. The methyldicyano- 

 glutarimide is a compound which, sublimed, crystallises in needles or prisms of m. p. 255 

 to 257°. As regards the descriptions of the other compounds prepared we have to 

 refer our readers to the original. 



R' R' R x /R' 



c c 



CN-HCj/NcH-CN CN-HCf Nc-CN CN-C.4- -4C-CW 



ocl Jco ocl Jco ocl Jco 



N N N 



I I I 



R" R" R" 



(I) Derivative of cyciodicyano- (II) Derivative of cycZodicyano- (III) Trimethylenepyrrole 



glutarimide. glutaconimide. derivative. 



In paper on 1 : 3-dimethylc2/dohexanone-2 K. v. Auwers and F. Krollpfeiffer 1 ), a 

 few years ago, drew attention to the point, that certain preparations like the numerous 

 hydro-aromatic polyalkylketOnes, which Haller 2 ) had prepared and described, had not 

 been pure compounds but mixtures. The authors showed then that in the methylation 

 of the l-methylc2/(/ohexanone-2, according to the method of Haller, far more of the 

 asymmetrical dimethyl derivative is formed than the statements of Haller would lead 

 one to suppose. Further, not only the asymmetrical dimethylc^/cfohexanone, as Haller 

 states, but also the symmetrical derivative will react with benzaldehyde. It followed 

 that the method of purification of Haller could not lead to the desired result. 



Without making any detailed reference to the justified criticism by v. Auwers, A. Haller 

 and R. Cornubert 3 ) have resumed their enquiry into the constitution of dimethylcyclo- 

 hexanone as prepared by the methylation of sodium-a-methylq/cZohexanone. They 

 produced in this way a very pure dimethylq/dohexanone (b. p. 170.5 to 171° [corrj; 

 d'-^ 0.9137; n D20 . 5O 1.4880; mol. refr. 36.92 [calc. 37.00]), the constants of which were in 

 accord with those which v. Auwers and Lange 4 ), Meerwein and Unkel 5 ), and v. Auwers and 

 Krollpfeiffer 6 ) had obtained, both in asymmetrical and symmetrical preparations. From 

 the ketone, a'-benzylidene-«:a-dimethyk?/cZohexanone (I, m. p. 82 to 82.5°) was obtained 

 by condensation with benzaldehyde in the presence of sodium ethylate, with a yield 

 of 26 per cent. This body being identical with the benzylidene compund which K. v. Auwers 

 and Krollpfeiffer had prepared from pure 1 : 1-dimethylq/c/ohexanone, it would follow 

 that Haller's dimethylcydohexanone must likewise be asymmetrical. 



They further attempted to effect the condensation of dimethylci/cZohexanone with 



benzaldehyde in another way, by means of gaseous hydrochloric acid, which v. Auwers 



,Qfl \ had likewise proposed. In this reaction they obtained, in 



CH 2 C addition to the benzylidene derivate described, a lemon 



/ \ yellow, oily benzylidene dimethylc^/dohexanone (b. p. 197 



CH 2 \ >CO 



to 198° [corr. 28 mm.]), and further two other, probably 

 CHjj C=CH— C 6 H 5 anomalous condensation products of 1 molecule of 

 (i) a'-benzyiidene-a : a-dimethyiq/do- dimethylcycfohexanone and 2 molecules of benzaldehyde 

 hexanone. (C 2 2H 24 2 , m. p. 117 to 118° and 188 to 190°). 



!) Berl. Berichte 48 (1915), 1226. — 2 ) Cf. Report April 1915, 97. — 3 ) Compt. rend. 170 (1920), 700. 

 l ) Liebig's Annalen 401 (1914), 303. — 5 ) Ibidem 376 (1910), 152. — 6 ) loc. cit. 



