/ 
NOTES ON SCIENTIFIC RESEARCH. 85 
obtained by reduction of «-thujamenthone in alcoholic solution with sodium, boiled at 
from 212 to 214°; digo 0.8990; np 1.4611. On oxidation with chromic acid, it regenerated 
the ketone; when heated with zinc chloride, it formed thujamenthene boiling between 
163 and 165°. The reduction of the oxime of «-thujamenthone in alcoholic solution 
with sodium led to e-thujamenthylamine (b. p. 196 to 197°), which on treatment with 
nitrous acid yielded, in a normal way, «-thujamenthol in addition to the hydrocarbon. 
In order to arrive at the @-thujamenthone, two ways may be chosen: either iso- 
thujone is reduced direct according to Skita with palladium chloride (PdCl,) and - 
hydrogen, or one starts from the pure oxime of isothujone, melting at 119 to 120°, 
reducing it in the presence of palladium and hydrogen. Thus is obtained, in scanty 
yield, it is true, the oxime of @-thujamenthone, which is decomposed on being heated 
with acids. It melts between 130 and 131°, the semicarbazone between 190 and 191°. 
The 8-thujamenthone regenerated from the latter melts at from 215 to 216.59; digo 0.8990; 
Np 1.4511. On heating with sulphuric and glacial acetic acids, the oxime of @-thuja- 
menthone is converted into an isooxime melting at 102°. @-Thujamenthol (obtained by 
reducing $-thujamenthone with sodium and alcohol) boiled at from 216.5 to 217.59; 
digo 0.8995; np 1.4583. It yielded again $-thujamenthone on oxidation with chromic 
acid. When heated with zinc chloride, @-thujamenthol passed into thujamenthene. By 
reduction with sodium and alcohol, the oxime of @-thujamenthone was converted into 
8-thujamenthylamine (b. p. 206.5°), the hydrochloride of which was subjected to the 
action of sodium nitrite, when a probably tertiary thujamenthol was formed (b. p. 204°). 
Dehydration of this thujamenthol led to another hydrocarbon than the dehydration 
of the two thujamenthols just described. Whereas the thujamenthenes from «- and 
8-thujamenthol do not form any solid nitrosochlorides, thujamenthene from tertiary 
thujamenthol affords a sparingly soluble, labile nitrosochloride melting at 108°. By 
splitting off hydrochloric acid it forms the oxime of zsothujone. The sequence of 
reactions indicated proves that »-thujamenthone may be reconverted into isothujone, 
from which it was prepared. 
Wallach considers «- and -thujamenthone as physically isomeric, but it has not 
been possible to establish anything which would point to the presence of chemical 
isomerism. The fact that the peed isomerides described show different boiling 
points is striking. 
As to the scission of santolinenone into the optical antipodes see p. 35 of this Report. 
Phenols and phenol ethers. 
The action of nitrosobenzene on phenol ethers. 
On p. 150 of our Report October 1911, we discussed a paper by ape Alessandri, 
and Pegna on the action of nitrosobenzene on unsaturated compounds. The study 
has meanwhile been continued by L. Alessandri*). He examined the action of nitroso- 
benzene on estragole, myristicin and methyleugenol, when three yellow compounds 
resulted, melting at 165°, 180° and 154°, respectively. Their constitution is probably 
analogous to that of the compound previously obtained from safrole. The action of nitroso- 
benzene on apiole goes on in a somewhat different manner; a yellow substance results 
(m. p. 137°) which probably represents the aldehyde (CHs O)2(CH2O2)C, H- CH: CH: CHO 
1) Atti Rk. Accaud. dei Lincei, Roma (5), 24 (1915), 62; Chem. Zentralbl. 1915, Il. 1210. 
