430 



pyrrole can be traiitsfonned iiilo C-derivatives by distillation tliioiigh 

 a red-hot tube. 



Ill all these intra-inoleciilar arrangements only one C-derivalive 

 was tbniid, whereaw it would be theoretically posRil)le ihat two 

 isomeric pyrroles would be formed, since the hydiocarbon rest 

 might be united at the it- or at the ji-carbon atom of the pyrrole 

 nucleus. 



From N-methyl pyrrole the ((-C-metliyl pyrrole was obtained by 

 PicTET. The structure of *(-C-melhyl pyrrole had already been deter- 

 mined by Zanetti, by converting this substance into the dioxiine of 

 levulic aldehyde. 



Pictb;t and Chépikux assume on grounds of analogy that in the 

 C-phenyl pyrrole which they obtained from N-plienyl-pyrrole, the 

 phenylgroup is united at the «carbon atom of the pyrrole nucleus, 

 and that the same thing holds for the C-pyridyl pyrrole (11), which 

 they obtained from N-ii(pyridyl)- pyrrole (I). A direct experimental 

 evidence, for this view was not given. 



As regards Pictet and Cbépieux' f?-pyridyl-«-pyrrole, the structure 

 which these investigators assign to it, is undoubtedly supported by 

 the fact that they have obtained nicotyrine (III) from this (?-pyridyl 

 pyrrole, as the structural formula (IV) of nicotine has been made 

 very probable by Pinnkh's re.searches. 



We found however that two isomeric (.-iiyridyl-pyroles are formed 

 in the transformation of N(«-pyridyl) pyrrole, one of which melts 

 at 93° and the other at 132 — 132.5 . This reaction must be 

 represented by the following scheme: 



CH 



HÜ/\CH 



(V) 



CH 

 HC/\CH 



^ilcH- 



HC\//C— n/" , 



HC\XC- 



N 



CH 

 HC^\CH 



HC- 



II 

 — C 



-CH 



II (VI) 

 CH 



NH 



HC\/C- 



N 



-C CH 



(VII) 



HC CH 



\/ 

 NH 



To which of our isomers formula VI applies and to which 



formula VII should be assigned, has not yet been established. It 



