— 134 — 



Like the ethylene oxides, these oxides also readily attach atom- 

 groups according to the following formulae: 



HBr __^— -* R,CHBr 'CH(OH).CH 3 



CH 3 .COBr 

 R.CH — CH.CH 3 - > R-CHBr.CH(OCOCH 3 ).CH 3 



\o- 



CH Q -COOH 



R.CH(OH).CH(OCOCH 3 ).CH 2 



The oxide oxygen atom therefore always remains linked to the 

 y8-carbon atom, as is also the case in converting the oxides by heating 

 or treatment with acids into ^-ketones R • CH 2 • CO • CH 3 . The bromine 

 atom of the side-chain in the a-position, in the addition products of 

 the oxides, is, as might be expected, very mobile; in fact in the 

 a-bromo-/?-oxy compounds so much so, that they decompose with 

 evolution of hydrogen bromide. 



With regard to the very rich experimental matter of these works, 

 we must refer to the original treatises. 



Nitrogenous bodies. 



The conversion of aldehydes and ketones into bases by boiling 

 with ammonium formate, has first been accomplished by Leuckart. 

 He obtained the formyl compounds of the primary, secondary and 

 tertiary bases corresponding to the crude material. O. Wallach has 

 applied this reaction already a long time ago to terpene ketones. 

 The occurrence of the mixture of bases and of the formyl compounds 

 as final products complicated the production of the bases in the pure 

 state, and for this reason Wallach 1 ) set himself the task of remov- 

 ing this defect in the reaction. If the formyl compounds were only 

 formed as secondary products from a primarily formed base and formic 

 acid, a lowering of the temperature should prevent the formation of 

 these compounds. This has in many cases proved to be feasible, 

 and has at the same time identified the formyl compounds as secon- 

 dary products of the reaction. The progress of the reaction could 

 now be explained as is expressed in the following formulae: — 



/OH 

 i. R 2 CO + NH 3 = R 2 C( 



X NH 2 



/OH /H 



2. R C< +HCOOH = R 2 C( +C0 2 + H 2 0, 



X NH 2 X NH 2 



in which formic acid represents the reducing agent. If then the 

 primary base has an opportunity of entering in reaction with a still 



1 ) Liebig's Annalen 343 (1905), 54. 



