154 PROCEEDINGS OP THE AMERICAN ACADEMY 



C 6 H 6 C=N C 6 H 5 -ON. 



, o c«h s -c.noh 



CsHs ^NHOH C « H »<0H C « H »*NOH 



a dioxime III. y dioxime IV. $ dioxirae V. 



The oximes I., II. and III.— V., respectively, can naturally be 

 converted into one another without molecular rearrangement by the 

 addition of water or halogen hydride, and the splitting off again 

 in a different way. The entire experimental work of Auwers, 

 V. Meyer, and others, on the oximes of benzil was very carefully 

 studied, and not a single fact found therein which could not be 

 explained by the above formula?, which are chemically different. 

 This shows on what an uncertain basis the assumed geometrical 

 isomerism of these substances rests.* 



A similar relationship exists in the case of the oximes of benz- 

 aldehyde : the a oxime is converted by means of hydrochloric acid, 

 as Beckmann f has shown, into a solid j3 isomer. 



It is highly probable, in the first place, that the product obtained 

 with hydrochloric acid is not a salt, but an addition product, 



/ H 

 C 6 H 5 C — N-OH. 



I H 



CI 



On pouring this into sodic carbonate, it loses HC1 in a different 



way forming the oxid, j C 6 H 5 -C-£THOH, or /? oxime. That a 



/\ 

 splitting off of HC1 can take place in this manner, and often 

 spontaneously, has been shown above (pp. 136, 150). 



The ready conversion of /3 benzaldoxime into benzonitrile is self- 

 evident in the case of the above oxid formula. Furthermore, the 

 simultaneous formation of nitrogen and oxygen ethers on treating 

 the ft oxime with alkyliodides § is also explained. 



That the two oximes of benzaldehyde both contain a hydroxyl 



* Cf. Claus, J. pr. Chemie, [2.], XLV. 1-20. 



t Ber. d. Chem. Ges., XXII. 430. 



t I propose the name oxid for the group -NHOH, leaving the name oxime 

 for the group =NOH : this is entirely analogous to the names hydrazide and 

 hydrazone for the groups (; H 5 NH-NH- and C, ; H 5 NH-N=, respectively. 



§ Goldschmidt, Ber. d. Chem. Ges., XXIII. 2176. 



