1919, meeting of July 18, p. 10. — 4) Cf. Report April 1905, 111. 
Bite © yu ieee Daiiat it s  ie WB RR reer fel of 
; aN rs Daa i eu tiha 4 iat 
136.3 REPORT OF SCHIMMEL & Co. APRIL/OCTOBER 1920. i 
Amongst the nisatieeeed hydroaromatic Rerones pulegone vielded 2 a nc , é 
a yellow oil (b. p. 148 to 150° at 13 mm.), and in addition varying amounts of two. 01 
compounds, which were regarded as addition products of aniline and ypulegone | 
pulegoneanil. Pulegone has a pair of conjugated double bonds ~+C:C-C:O, and i 
known that by the action of an amine on such a system, the amine is frequently added 
on with rupture of the double bond. A complete splitting of pulegone-anil into 2-methyl- 
cyclohexanoneanil and acetoneanil was, however, not observed. In contrast to pulegone, wehe 
dihydrocarvone and carvone yielded anils (yellow oils, b. p. 170 to 171° at 15 mm. mae 
b. p. 180 to 182° at 17 mm.) without the formation of noteworthy by-products. With 
aniline hydrochloride as condensing agent camphoranil was obtained, a bright yellow, 
almost odourless oil (m. p. 13.59, b. p..164.5 to 166° at 15 mm.). It was quickly ene ts 
up into camphor and aniline by dilute acid. oS 
The anils of the unsaturated hydroaromatic ketones in Asha acid solution eet NY 
a deep blue coloration with nitric acid, the same with nitrites, chlorates, chromates and a 
hydrogen peroxide. Cyclohexanoneanil, menthoneanil and camphoranil, show no, or else 
a very slight coloration. CHE nay a 
G. Reddelien*) has obtained condensation products of benzophenone with p-aminoazo- — 
benzene, by heating benzophenone-anil (CsH;)2C = NC,H; with p-aminoazobenzene in the ig : 
presence of some aminoazobenzene hydrobromide at 170 to 180°, and then further heating | 
in vacuum to 230°. The resulting diphenylmethylene-p-aminoazobenzene, m. p.123°,was 
a magnificent crystalline orange-yellow substance possessing strong dichroism. Analog- — 
ously, the diphenylenemethylene-p-aminoazobenzene (m. p. 141—142°, orange-coloured 
needles also strongly dichroic) was produced from fluorenoneanil. In addition, Reddelien i 
prepared a few aldehyde-p-aminoazobenzenes. P 
As with the ketone anils, the salt formation of these compounds was accom. 
panied by phenomena of halochromism. The halochromism was intensified if. the 
C:N group was conjugated with a neighbouring C:C group, such as with cinnamylidene- a 
aminoazobenzene. i 
Ne a So ee ee ee a oe ae 
Thujone.—By reduction of sabinol with sodium in amylalcoholic solution Semmler_ . 
obtained an alcohol, which on oxidation yielded «a @-thujone, which was not further — 
characterized”). If sabinol is reduced in another way, a lazvorotatory thujone can be 
obtained from the alcohol. Wallach*) caused free hydrogen to act on sabinol in the ~ 
presence of palladium chloride and obtained, in addition to hydrocarbons, a lavorotatory ue 
secondary alcohol, which on careful oxidation yielded chiefly /-thujone. The ketone | 
had the following properties: —. b. p. 203 to 205° at ordinary pressure, deo0 risk a 
[<p] — 30.62° (16 per cent. solution in methyl alcohol); np 1.4507. i 
Since its rotatory power considerably exceeds that of a previous preparation Be 
tained from thuja oil (@) —10.23°)*), it must still remain undecided whether a third 
modification of thujone is present, whose existence had already been earlier indicated, 
but has not yet been proved. The above preparation yielded a fluid oxime, which o 
long standing showed signs of crystallising, by the appearance of slight deposits, but 
which also contained small quantities of §-thujone. ae 
Thujone-containing oils, which have been kept for a long time, show a greater 
less content of «-thujaketonic acid CioHigO3. This acid was identified in old stocks 
sage oil, and in fractions consisting essentially of thujone of: — thuja, tansy, 
1) Berl. Berichte 58 (1920), 340. — 2) Cf. Report October 1900, 73. — *) Nachr. K. Ges. W. 
