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138 “REPORT OF SCHIMMEL & Co. APRIL 1914, Bia iain 
which, when heated with solid potassium hydroxide in the presence of platinised pieces 
of porous tile is converted into phenylcyclopropane (II). The last-named body boils at 
173,6°; d®>0,9401; n 1,5342. When left 
CsHs:- CH — CHe standin with Shacehielen sul Rigas: 
| | C,H;-CH—CH, g suerte 
HN CH Was it polymerises into a solid mass; if shaken 
O74 CH: for two days with dilute sulphuric acid it 
Nes is converted into a dimeric phenylcyclo- 
(I) Phenylpyrazoline. (Il) Phenylcyclopropane. propane, Cis Heo; _b. p. 330 to BEAD dy 1,002. 
Ketones. 
Methylheptenone. In continuation of their earlier investigations, G. Ciamician 
and P. Silber’) have studied the action of light upon methyl heptenone (I). The ketone 
was exposed to light from the end of May to the beginning of November in a capacious 
flask filled with oxygen. When the flask was opened a considerable vacuum was 
apparent, and instead of oxygen the vessel was found to contain carbon dioxide. A 
reaction-mass had been formed in the shape of a yellowish, strongly acid solution, 
from which acetone (bromophenyl hydrazone, m. p. 93 to 94°) was isolated. The 
solution was rendered alkaline with potash and extracted with ether, the result being 
a keto glycol (Il) and possibly also a hydroxydiketone (Ill). For the purpose of iden- 
tifying the latter it was converted into the diketone (CHs),2CH-CO-CH2-CH2-CO-CHs 
by boiling with dilute sulphuric acid. The semicarbazone and the dioxime gave 
approximately the correct m.p. In the alkaline solution, when extracted with ether, 
and acidulated, formic acid, acetic acid, and lzvulic acid were found. 
(I) (CHs)2C: CH: CH2:CHs:CO-CHs (II) (CHs)2C (OH): CH(OH)- CH2: CH: CO- CHs 
Methylheptenone. Ketone glycol. 
Hydroxydiketone. 
Santenone. Some time ago we referred to a publication by Rimini’) on santenone, 
in which a new isomeride, ‘sosantenone, was described. From its behaviour towards 
permanganate isosantenone would appear to be an unsaturated body, but in reality, as 
has now been established, it is saturated, as Rimini?) has discovered subsequently that 
the reaction of isosantenone with permanganate was caused by traces of impurities 
with powerful reducing-properties. For purposes of purification, the isosantenone was 
diluted with a 2p.c. potassium permanganate solution under ice-cooling. The semi- 
carbazone obtained from this product melts at 175° and, when decomposing, yields 
isosantenone, m. p. 185 to 186°. Jsosantenone oxime constitutes a syrupy oil, b. p. 
155 to 164° (28 mm.). Unlike santenone oxime, it readily reforms isosantenone when 
brought to boil with dilute sulphuric acid. Rimini also describes dibromo-isosantenone, 
as well as the oxidation of isosantenone. When treated with potassium permanganate 
in alkaline solution at ordinary temperature a syrupy compound C,Hi,CO-CO2H, is 
formed which, when heated with lead peroxide in glacial acetic acid solution, gives 
off carbon dioxide. The semicarbazone of the oxidation-product melts at 1969. Oxi- 
dation of isosantenone with potassium permanganate in alkaline solution in the warm, 
1) Berl, Berichte 46 (1913), 3077; comp. Report October 1911, 122. — *) Comp. Report April 1912, 185. — 
3) Gazz. chim. ital. 48, I (1913), 522; R. I. Lombardo di Scienze e Lettere 46 (1913), 787 ae forwarded 
to us by the author); Chem. Zentralbl. 1918, II. 1390. Jit 
