a 
NOTES ON SCIENTIFIC RESEARCH. . 99 
C. Agostinelli*) heated an alcoholic solution of thujone with ammonium hydrogen 
sulphide for 24 hours in a sealed tube up to 150° and obtained a brown, somewhat 
viscid mass, from which isothujone (as oxime or semicarbazone, respectively) and 
thiotsothujone, C:oHisS, could be isolated. The isomerization of thujone is due most 
likely to the hydrogen sulphide, as it likewise occurs on heating with ammonium ° 
hydrogen sulphide to 60°. From ‘sothujone and ammonium hydrogen sulphide also 
only impure thio?sothujone formed. 
There are, in consequence, two phases of action of armmonium hydrogen sulphide 
on thujone: in the first the isomerization to isothujone takes place; in the second, this 
is converted into a mixture of polysulphides, in which only the presence of thio- 
isothujone could be proved. 
Carone. By heating carone with ammonium hydrogen sulphide under pressure, 
C. Agostinelli*) obtained a mixture, which was separated into fractions by steam 
distillation. From the volatile part, a body of the formula (CioHi7)2S2 was isolated; 
_m.p. 238 to 242°. The residue which remained after distillation with steam, a dark 
red oil, decomposed between 80 and 90°. The contents of sulphur pointed to a pen- 
tasulphide, Cio Hes Ss. 
Carvone. Some years back, G. Ciamician and P. Silber’) obtained on exposure of 
carvone to the light an isomeric body (m. p. 100°; b. p. 206,5°), which showed great 
similarity with camphor. E. Sernagiotto*) investigated this compound more closely 
and suggests for it the name of carvonecamphor. The oxidation with potassium 
permanganate led to a dibasic acid, CioHisO.u, melting at 174°, and a ketonic acid, 
C,Hi2O3, melting at 100°, which latter can also be obtained from the dibasic acid 
by means of potassium permanganate. The ketonic acid is characterized by a phenyl- 
hydrazone melting at 176° and an oxime melting at 107°. When being treated with 
alcoholic sulphuric acid, carvonecamphor yields isocarvonecamphor, an oil boiling 
between 222 and 224°. The oxime melts at 167°; the semicarbazone, at 209°. Through 
reduction with palladium and hydrogen, dihydrovsocarvonecamphor results, an oil 
boiling at 224°. 
If carvonecamphor is reduced with sodium and alcohol, carvoneborneol forms 
(m. p. 135°; b. p. 214°), which by oxidation with Beckmann’s chromic acid mixture may 
be reconverted into carvonecamphor, which under the action of the oxidizing mixture 
partly isomerizes to isocarvonecamphor. 
H. Rupe and W. Tomi?*) report on some high molecular, optically active hydro- 
carbons and ketones derived from carvone. From magnesium phenyl bromide and 
carvone, they obtained 2-phenyl-p-menthadien-6, 8 (9)-ol-2 (2-phenylcarveol), a liquid 
boiling at 164,5 to 165,5° (10 mm.). In order to prepare 2-phenyl-p-menthatriene-2, 6,8 (9), 
the authors added the ethereal solution of the addition product of magnesium phenyl © 
bromide and carvone in drops and under cooling to 30 p.c. sulphuric acid. The 
resulting hydrocarbon boiled at 149 to 150° (10 mm.); @p,;0 65,32°. Klages °) observed 
at the time the boiling point of 159 to 100° for phenylcarveol (12 mm.) and + 110,2° 
as highest optical rotation for phenylmenthatriene. It is therefore doubtful whether we 
1) Gazz. chim. ital. 44 (1914), Il. 111; Chem. Zentralbl. 1914, Il. 1438. — *) Gazz. chim. ital. 44 (1914), 
Hl. 111; Chem. Zentralbl. 1914, Il. 1439. — #4) Berl. Berichte 41 (1908), 1931; Report November 1908, 159. — 
*) Atti R. Accad. dei Lincei, Roma (5) 23 (1914), I. 70; Chem. Zentralbl. 1914, II. 1398. — 5) Berl. Berichte 
47 (1914), 3064. — *%) Berl. Berichte 89 (1906), 2306; Report October 1906, 131. 
7* 
