69 



methyl alcohol, of a nitrosochloride, and of a chloric hydrate, but 

 could not obtain a crystalline product anywhere. Nor did oxidation 

 with potassium manganate according to Wagnkr ^) lead to a result; 

 the only products that could be identified were acetone and oxalic 

 acid ; hence I must rest satisfied with the communication that with 

 generation of methane a mixture of hydrocarbons CipH,, is formed. 



With C2H5MgBr the reaction takes place much less vigorously, 

 and chiefly unchanged cineol distills over; the diminution of the 

 specific gravity, as well as the reduction of an ammoniacal silver oxide 

 solution pointed, however, to the presence of hydrocarbons OioH^g. 



The action of CgH.MgBr proceeds quite differently ; it is true, 

 here too an addition product is formed, but this remains unchanged 

 on being heated, even up to 200°, so that when treating it we get 

 back the cineol, besides diphenyl. Perhaps that here an intramole- 

 cular conversion may be obtained on continued action in the cold, 

 for then crystals separate from the etheric solution of cineol and 

 C6H5MgBr ; if these crystals are treated separately, a little (3 grammes 

 from 42 Gr. CgHsMgBr and 36 Gr. cineol after 3 months' standing) 

 of a liquid that goes over between 80° and 90° at 21 mm., which 

 with phenylisocyanate gave no crystalline urethane. The liquid which 

 was poured off the crystals, yielded nothing but cineol. 



With regard to the reduction of internal oxides according to the 

 method of Sabatier and Senderens, there exists in the literature 

 only one example, viz. the reduction of cyclohexene oxide to cyclo- 

 hexanol ^), in which the yield was even quantitative. Besides Sabatier'') 

 expressed the opinion that all the ethylene oxides could be hydrated 

 according to his method. 



I could not get a reduction for cineol in this way; when at 170° 

 this substance with an excess of hydrogen had been led twice 

 through a tube 40 cm. long, filled with pumice nickel, the sp. gr. 

 had not changed in the least. 



These researches, both with cineol and with other oxides, are 

 being continued. 



Utrecht. Org. Chem. Lab. of the university. 



1) VVagneb, B. B. 23, 2315 (1896). 



2) Brunel, Ann. Chim. Phys. (8) 6, 237 (1905). 



^) Sabatier, Die Katalyse in der organischen Chemie Leipzig 1915, pag. 80. 



