182 



UNIVEUSITY OF COLORADO STUDIES 



by one bond, two bonds are attached to carbons of separate quinoline 

 molecules, and the fourth bond is satisfied through a hydrogen atom. 

 This hydrogen atom is not replaceable by acetyl or bromine; the 

 sulphur has however the power of becoming hexavalent and adding 

 two atoms of bromine, a molecule of nitric acid, and in combination 

 with the second sulphur atom a molecule of sulphuric acid. A sim- 

 ilar phenomenon was observed bySaytzeff' and Beckman"^ in the case 

 of sulphoxides. These substances can also add a molecule of nitric 

 acid, thus one can obtain, for instance, the compound (CHj)^ 

 SO • HNO.,. Colby and McLaughlin' obtained when nitrating 

 (CJIA2 SO, besides two nitro bodies, a by-product which was very 

 similar to the above mentioned dimethylsulphoxide nitrate, and which 

 probably was a diphenylsulphoxide nitrate. 



Paratoluthiochinanthrene shows analagous properties to the first 

 of the series, and like it is not sensitive to oxidizing or reducing 

 agents; SOL by the reaction gives, as with quinoline, besides the 

 sulphur base, chlorine substitution products. A monochlorine body 

 was in this case however not obtained. Here di and trichlor bodies 

 were formed. The reaction appears in a much clearer light than 

 before. A molecule of S.Clj acts upon two molecules of quinoline 

 in the following manner: First, two atoms of hydrogen, one from 

 each quinoline molecule, unite with two atoms of chlorine from the 

 chloride, forming hydrochloric acid ; the neighboring hydrogen atoms 

 in the quinoline molecules then change over to the sulphur atoms, 

 leaving each a carbon valence to be satisfied with the fourth sulphur 

 valence. 



(1) Liebigs Annalen der Chemie, 144. 148. 



(2) Journal Prakt. Chemie. 17, 471. 

 ( >) Berliner Berichte. 20, 198. 



