108 REPORT OF SCHIMMEL § Co. OCTOBER 1914/APRIL 1915. 
lauronic acid, wick they converted with the aid of tion chloride, inte the chloriale® = 
melting at 99°, They obtained cyanolauronic acid by saponifying the crude chlorid ee 
When reducing the nitrile of camphoceenic acid with palladium and hydrogen, campho- — 
ceanic acid nitrile (m. p. 28 to 30°) resulted, which on saponification was transteca er 
into camphoceanic acid. . ‘ 
Oxydes. 
On page 13, we have reported on dicitronelloxide, GisFeOr 
Nitrogenous Bodies. 
We mentioned at the time the conversion of the hydrazine compounds of citral 
and citronellal, as described by N. Kishner*), and can now give further details con- 
cerning this reaction. Kishner*) resolved a hydrocarbon, which he had obtained on 
heating citralhydrazone with potassium hydroxide, into two fractions boiling at 162 to 
163 and 163 to 165° (760 mm.), respectively. These hydrocarbons correspond perhaps 
with the limonene and terpinolene forms of citral. When shaken with fuming hydro- 
bromic acid the lower boiling hydrocarbon forms a compound which is isomeric 
with the raw material, viz., linaloolene, CioHis. By reduction according to Sabatier 
it is converted into i-2,6-dimethyl octane, CioHe2, melting at 159,5° (776 mm.). d-2,6-di- 
methyl octane results on reduction of the hydrocarbon, obtained from the hydrazone 
of citronellal. 
W. Schneider together with D. Clibbens, G. Htllweck, W. Steibelt and F. Wrede*) 
continued, his work on mustard oils and allied bodies*). He now reports on thiou- 
rethanes and thiourethane ethers from some natural mustard oils, synthetic glucosides 
from thiourethanes, the addition of phenol to mustard oils and on the phenyl- - 
thiourethane-d-glucoside. They carried out the transformation of the silver allylthio- 
carbaminate with different halogen alkyls and further prepared a number of homologous 
and isomeric allyliminothiolcarbonates from the addition products of methyl and propyl 
alcohols with allyl mustard oil, obtaining as an intermediate stage the silver salts of 
these thiourethanes, which had not been described so far. Experiments were made as 
to the behaviour of allyliminothiolcarbonate towards silver nitrate and towards myrosine, 
as this ester has in its constitution certain relation to Gadamer’s formula for sinigrine®). 
Myrosine does not influence the ester; silver nitrate decomposes it, but in a compli- 
cated way, under the formation of a mixture of insoluble silver salts, the principal — 
constituent of which seems to be mercaptane silver. Further, thiourethanes of benzyl- 
mustard oil and of cheiroline®) were prepared. In order to obtain benzylthiourethane 
(ethylbenzylthiocarbaminate, C,H;-CH.-NH-CS-OC;Hs), 15 g. of benzyl mustard oil 
were heated in a tube for 6 hours up to 120 to 130° with 80 cc. of alcohol. With a 
view to obtaining the thiourethane quite pure, it must be distilled in an extreme 
vacuum. It boils at from 125 to 130° (0,3 to 0,4 mm.); the silver salt melts. at 179°. 
If this salt is boiled with ethyl iodide, it affords diethylbenzyliminothiolcarbonate, 3 
CsH;-CH2-N:C(SC.H;)(OC:H;), boiling at 164 to 165° (18 mm.). When heated under 
pressure with absolute alcohol cheiroline forms a thiourethane, melting at 71°, wz., k 
1) Comp. Report April 1912, 195. — 2) Journ. russ phys. chem. Ges. 45 (1913), 1779; Chem. Zentralbl. 1914, 
I. 1497. — %) Berl. Berichte 47 (1914), 1248, 1258, 2038, 2218. — +) Comp. Report October 1910, 85;°Aprib 
1918, 107, 151; April 1914, 98. — 5) Comp. Report April 1913, 151. — *) Cheiroline is the sulfonic mustard | P 
oil occuring in wallflower seeds. 
