CH 2 



1 



• CH 2 -CH 2 • NH 2 







CH, 



. CH 2 .CH 2 OH 









CH 2 

 = H 9 0+ 1 



•CH 2 



•CH 9 



• CH • NH C 



1 

 •CH, 



— 129 — 



point 134 to 138 ; d 0,863; n D2 4 M575J melting point of the hydro- 

 chloride 203 to 204 , of the benzoyl compound 149 , the urea 195 

 to 196 ) could be separated off. The hexamethylenimine which might 

 be expected could not be isolated. As only pure isoxime free from 

 oxime was used, the occurrence of cyclohexylamine can only be ex- 

 plained by ring-disruption and new ring-formation in the following 

 manner: — 



C H 2 • C H 2 • C H 2 v 

 I >NH + H 2 



CH 2 - CH 2 • CO/ 



hexanone isoxime 



cyclohexylamine. 



Wallach mentions further the conditions under which the nitroso- 

 chloride of cyclohexene (tetrahydrobenzene) which had already been 

 obtained in small quantity by Baeyer, is produced in a better yield. 

 It has not yet been possible to convert this nitrosochloride in the 

 still unknown oxime of hexenone. 



In an analogous manner to methyl cyclohexanone 1 ), Wallach 

 obtained by the action of bromoacetic ester on cyclohexanone in the 

 presence of zinc or magnesium, cyclohexanol acetic ester: — 



7 OH 

 CH 2 -CH 2 .C< 

 I |\CH 2 C0 2 C 2 H 5 



CH 2 • CH 2 • CH 2 



This body is converted by loss of water into cyclohexene acetic 

 ester, and the latter by saponification into cyclohexene acetic acid, 

 which melts at 37 to 3 8°, and boils at 140 at 12 mm. pressure. 

 By adding bromine it yields a brominated acid (melting point 1 1 9 

 to 120 ), and on oxidation with potassium permanganate in a weak 

 alkaline solution, an oil with a hexanone-like odour, whose semi- 

 carbazone melts at 203 to 204 °. The analysis points to a compound 

 with seven carbon atoms, which, however, possesses the character of 

 an aldehyde. 



Acetylcyclohexanone. George Leser 2 ) has obtained by con- 

 densation of cyclohexanone and acetic ester by means of sodium, in 

 a fairly good yield, acetylcyclohexanone, a liquid with a pene- 

 trating odour, which boils at in to 112 at 18 mm. pressure; 

 d o 1,0782; n D 1,51384. 



1 ) Liebig's Annalen 314 (1900), 151. Report April 1901, 61. 



2 ) Compt. rend. 141 (1905), 1032. 



