1190 



57°— 58° (the m.p. of a mixture was also 57°— 58°); the identity 

 of the resulting samples of ,i-hydrindone moreover appeared from 

 the concurring m.p. of the three oximes. We did not get any in- 

 dication of the possible formation of «-hydrindone. 



The isomerisation of indene oxide to ivhydrindone also takes place 

 when water is absent, viz. in a dry ethereal solution by means of 

 some anhydrous zinc chloride; therefore we are not inclined to 

 accept the intermediate formation of one of the glycols during the 

 conversion of the oxide to /-J-hydrindone. 



(?-Hydrindone has a very pleasant odour, resembling thai of the 

 methylesler of anthranilic acid; by its scent we could observe the 

 ketone as a by-product from many reactions, mostly in acid but 

 also in alcaline solutions. 



Hydration of inde?ie oxide. 



When it is attempted (o add the elements of water to the oxide, 

 nearly always the odour of ,Miydrindone distinctly appeal's and in 

 fact we could in several cases isolate the ketone by steamdistillation. 

 Besides, a poorly soluble condensation product is always formed, 

 which we consider to be anhydro-bis-,M)ydrindone, for this com- 

 pound has been obtained by Heusler and Schieffer from li-hydrindone 

 by the action of diluted acid or of a solution of sodium hydroxide 

 as well. 



However, the hydration may be conducted in such a way {viz. 

 in a very diluted aqueous solution) as to limit the rearrangement 

 into ^Miydrindone; besides, not only cis-, but also an important 

 quantity of t r an s-hydrindene diol is always formed, in which 

 latter case obviously a change of the configuration must have occurred. 



This result places in a very dubious light the determination of the 

 configuration of the cis- and trans-cyclohexane-1.2.diols '), naphtane- 

 2.3.diols '), iiaphtatriene-2.3.diols ') and cyclopentane-1.2.diols '), since 

 it was based on the assumption that the cis-configuration belongs to 

 the glycol, which proceeds from the addition of water to the oxide. 



(We perceive that W. Lossen, Niehrenheim and Dueck^) think they 

 have obtained a mixture of raceraic acid and of mesotartaric acid 



.CH . COOH 



from ethylene-oxide-«-|?-dicarboxylic acid 



; still it is pos- 

 CH . COOH 



M L. BRUNEL-Ann de Chim. et de Phys. (8) 6. 280 (1905). 



2) H. LEROux-ibid. (8) 21, 496 and 500 (1910). 



3) H. LEROUx-ibid. (8) 21, 511 (1910). 



*) M. GoDGHOT and Taboury-BuU. Soc. Chim. (4) 13, 535—42 (1913). 

 5) W. Lossen, c.s.-Leb. Ann. 348, 305 (1906) 



