NOTES ON SCIENTIFIC RESEARCH. 81 
alcohol and activated nickel, was thus reduced already in the cold with formation 
of methylphenyl propionate (b. p. 237 to 238°). From 60 to 80° anethole yielded 
p-methoxypropylbenzene. Eugenol, safrole and isoeugenol were likewise reduced, iso- 
eugenol giving the same reduction-product as eugenol. 
In their 8th communication on synthesis in organic chemistry, E. Paterno, G. Chieffi 
and G. Perret) describe some experiments, which we intend mentioning briefly. Aceto- 
phenone and benzyl alcohol yielded on exposure to the light «, 6-diphenylpropane glycol, 
an oil of light yellow colour. Only small quantities of hydroanisoin could be isolated 
from the products obtained by exposing anisaldehyde and toluene to the light; 
saligenin and benzophenone gave only benzopinacone, in addition to the unaffected 
part of the original material, whereas saligenin and acetophenone probably yielded 
salireton, Ci,Hi2O3. With toluene as well as with acetophenone heliotropin (piperonal) 
forms colourless crystals melting at 226 to 228°. 
S 
In a series of articles, E. Erlenmeyer’) deals with the activation of cinnamic acid 
and benzaldehyde by asymmetric induction, i.e. by boiling the substances in buestion 
with an alcoholic solution of tartaric acid. He believes that in this way he can obtain 
optically active cinnamic acid and optically active benzaldehyde. As for benzaldehyde, 
E. Wedekind?) is of opinion that the alleged activation is to be explained by an optic- 
ally active impurity, presumably a kind of acetal combination of tartaric acid with 
benzaldehyde. 
Phosphorites and phosphorates. 
In a treatise on the behaviour of unsaturated compounds towards phosphorus and 
oxygen, R. Willstatter and E. Sonnenfeld‘) describe a new class of compounds, which 
they call phosphorites and phosphorates, because they are built up in an analogous 
way as nitrosites and nitrosates. They form on shaking the solutions of unsaturated 
compounds (amylene, menthene, pinene, cinnamates, 8c.) in benzene or cyclohexane 
under the exclusion of moisture with finely divided white phosphorus. For this purpose 
the authors constructed a special shaking apparatus, which is connected with an 
oxygen generator. The double linking thus takes up P.,Q,, with the exception of that 
of allyl alcohol, which yielded a combination of the formula (C3;H,O)3P,0.. The speed 
of the reaction slackens suddenly after the absorption of three atoms of oxygen, the 
fourth atom being added about six times more slowly. If the reaction is interrupted, 
e.g. that of 1 molecule of cyclohexane with 2 atoms of phosphorus after 3 atoms of 
oxygen have been absorbed, one finds that a product of the formula CgHioP2Os, a ° 
phosphorite, has formed; on further absorption of oxygen, the phosphorate, CsHioP2Ox:, 
results. 
In this way pinene furnishes pinene phosphorate, CioHigP:O., a slightly yellow, 
crystalline, remarkably hygroscopic substance of a not unpleasant odour, reminding 
of fir resin. It still remains to be ascertained whether the compound described by 
Sieburg*) as terpenol hypophosphorous acid is identical with it. Menthene forms a 
phosphorate, CioHisP2O., a yellowish white, fairly hygroscopic powder. Cinnamic acid 
ester reacts with phosphorus and oxygen as violently as the unsaturated hydrocarbons. 
2) Gazz. chim. ital. 44, I. (1914), 151; Chem. Zentralbl. 1914, I. 2150. — *) Biochem. Zeitschr. 64 (1914), 
2%, 366, 382; 66 (1914), 509; Chem. Zentralbl. 1914, I]. 1230. — *%) Berl. Berichte 47 (1914), 3172. — 4) Berl. 
Berichte 47 (1914), 2801. — 5) Biochem. Zeitschr. 48 (1912), 280; Report April 19138, 98, 
6 
