337 



oxide CgHijO was prepared. We used for this purpose an appaiatus 

 as indicated by Skita '), in which the process of the reaction can 

 be easil}' followed. During the fractionation tiie sul)stance polymerizes 

 partially, so that a [)erfectly pure product only can be obtained 

 at the expense of considerable loss. 



In spite of caieful purification the possibility exists therefore that 

 a small quantity of unsaturated product is left behind. 



The substance was optically inactive, and showed the following 

 constants : 



bp. 103°— 106° dj« 0.8693 n^ 1.42797 



(analysis: found C71.8 H12,3; calc. 72,0 H12,0). 



In the way indicated by Lipp loc. cit. we have further prepared 

 the (f-hexylene oxide, with the following constants: 



bp,6, 106°— 106°. 2, d|^ 0.8617, n^ 1.41887. 



Since on reduction «-vinyldihydrofurane must yield y-hexylene oxide, 

 we have also prepared this oxide according to Wohlgemuth *), who 

 however, only gives its boiling-point, viz. 106° — 108° at 770 mm. 



The following constants were found : Bpy,„ 106°.5— 107°, dj^ 0.8609, 

 n^, 1.41685. 



The corresponding bromides were obtained by treatment of these 

 oxides with the 8-iO-fold volume of hydrobromic acid (48 '/J in a 

 sealed tube for 1 to 2 hours at 100°. The 1-5-dibromo hexane boiled 

 at 15 mm. at 105°— 108° (analysis found Br. 65.3 7, calc. 65.5), the 

 1-4-dibromo hexane at 106°— 108° at 15 mm. (Br. found 65.4). The 

 boiling-point of the di-l)romide obtained from the reduced oxide OjHi,0 

 was 106°— 110° at 14 mm. (Br. found 65.6). It is evident that from 

 the equation of the physical constants, both of the oxides and of 

 their di-bromides, no conclusion can be drawn about the structure 

 of the reduced oxide CgHj,0, unless there are large quantities of 

 the substances at our disposal. It was, therefore, necessary to try 

 to obtain crystallized compounds. An attempt to prepare crystallized 

 benzoates of the glycols corresponding with the dibromides did not 

 meet with success. The action of piperidine on the di-bromides, on 

 the other hand, in which quaternary ammonium bromides were formed, 

 had a favourable result. 



In analogy with von Braun'), who made act I-5-dibromo pentane 



I) B. 45, 3595 (1912). 

 ') C.r. 159, 80 (1914). 

 S) B. 39, 4347 (1906). 



