- I 7 8 - 



fairly well menthol, d-menthylamine nitrite chiefly menthene. For this 

 reason the study of the cyclyl methylamines obtained from the cyclyl acetic 

 acids 1 ) according to well-known methods, was of interest. The 

 examination showed that the nitrites of these bases can be boiled 

 practically without decomposition in neutral aqueous solution, and that 

 by acidifying with acetic acid, there is formed, in addition to hydro- 

 carbons and the corresponding alcohols, an alcohol of the next 

 higher ring-system, which can be oxidised to the corresponding 

 ketone. In this manner the author succeeded in converting cyclo- 

 pentylamine into cyclohexanone, cyclohexylmethylamine into cyclohep- 

 tanone (suberone), and cycloheptylmethylamine into cyclooctanone 

 (azelain ketone). The last-named body, which has not yet been described, 

 and which has an odour somewhat like oil of bitter almonds, 

 CtL — CH — CH 2 — CO 



1 N ' 



C H 2 — C H 2 — C H 2 — C Hg 

 has the following properties: m. p. 25 to 26°; b. p. 195 to 197 ; 

 d2o° 0,9581; n i> 1,4694; m. p. of the semicarbazone 163 to 164,5°. 

 Wallach explains the conversion, for example, of cyclopentyl- 

 methylamine into cyclohexanol, in the following manner: — 

 C H 2 — C H 2 v C H 2 — C H 2 v 



i )ch.ch 2 .nh 2 .n0 2 h -> i )ch.ch r n 2 oh 



ch 2 -ch/ ch 2 -ch 2 / 



C H 2 — C H 2 v 



CH 2 -CH / - \ CH 2 + N 2 + H 2 0. 



The tricyclic ring formed can be split up hydrolytically in three ways : — 



CH 2 -CH 2 \ CH 2 - CH 2 CH 2 



I. ! CH \ + 11,0 = ' I 



CH 2 -CH- \CH 2 CH 2 — CH(OH) — CH 2 



Cyclohexanol 



II. CH 9 — CM 2 v CH 2 — CH,\ 



I " >CH-CH 2 OH-> I ' " >C = CH 



CH 2 ~CH 2V jS* CH 2 -CH 2 / CH 2 -CH/ 



I / CH \ + H 2 



CH 2 -CH /-|^CH 2 \ C H 2 CH 2 CH 2 _CH 



' I >CH.CH 3 -> I }C.CH 3 



III. CH 2 — CH(OHK CH 2 — CH^ 



In formulae II and III, where the tricyclic ring is assumed to be split 

 up at linking 2 or 3, the secondary products formed on decomposition 

 of the nitrites, a primary and secondary alcohol of the same ring- 

 system, and also the corresponding hydrocarbons, are reproduced, a 



x ) Comp. the present Report p. 173. 



J.J. Weber, Leipzig. 



1 



