— 92 — 
formed, in addition to an optically inactive alcohol CjoHgoO with 
a terpineol-like odour, a hydrocarbon C^o^ig^ which in view of its 
origin must be considered as zl^' or still more probably as 
^(^9)-menthadiene: 
C CHg CI H3 CHg 
The hydrocarbon is dextrorotatory, like citronellal; it boils at 9 mm 
pressure between 75^ and 80°, and has the specific gravity 0,8491. 
Its odour is said to remind of anise and star-anise, but at the same 
time also somewhat of fennel. 
Ketones. 
Wallach^) has communicated a very interesting treatise on the 
conversion of cyclic ketones into alkamines and into non-oxygenous 
bases of nitrogenous cyclic systems. 
The same investigator has already shown on a previous occasion, 
that the oximes of cyclic ketones, on conversiop into the so-called 
isoximes, suffer a molecular rearrangement, with formation of compounds 
which may be considered as anhydrides of acid amides (lactams), and 
that in this manner it is possible to arrive partly at already known, and 
partly at new nitrogenous heterocyclic compounds ^j. Thus pentanone 
oxime is converted into a-piperidone : 
CH2 • ^-^2\ ' ^-^2 * CO 
I \C:NOH > I I 
cu^'Cn/ CH2.CH2.NH, 
whilst from cyclohexanone and cycloheptanone oximes in a corre- 
sponding manner heterocyclic compounds with seven or eight members 
can be obtained. 
These isoximes or lactams are now susceptible to direct reduction, 
preferably by the application of amyl alcohol and sodium, and it is 
thereby possible to arrive at non-oxygenous bases of nitrogenous cyclic 
^) Liebig's Annalen 324 (1902), 281. 
^) Compare Report October 1900, 74. 
