236 Dr. A. W. Hofmann on the Phosphorus Bases. [Mar. 21, 



HO] 



Orthophosphoric acid HO > PO. 



HO J 



Ethylphosphinic acid HO [ PO. 



HO J 



Diethvlphosphinic acid C, H 5 > PO. 



HO J 



C 2 H 5 ] 



Triethylphosphinic oxide C 2 H 5 V PO. 



c 2 hJ 



V. Aromatic Phosphines. 



The well-defined results which the easy and handy use of phosphonium 

 iodide, as a source of phosphorus compounds, has furnished in the methyl 

 and ethyl series, and, as I shortly intend to communicate to the Society, 

 also in the propyl, butyl, and amyl series, very naturally created the wish 

 of extending these researches also to the aromatic phosphines. It ap- 

 peared especially worthy of interest to study an aniline with phos- 

 phorus in the place of nitrogen, — in other terms, phenyl phosphine and, 

 indeed, the whole series of phenylated phosphorus bases. I have instituted 

 many experiments in the hope of obtaining these bodies, but as yet with- 

 out success. Considering the remarkable inactivity of benzol chloride and 

 analogous benzol compounds under the influence of ammonia, I could 

 scarcely hope to form phenylphosphine by acting on phosphonium iodide 

 with benzol chloride. Nevertheless the experiment was made ; but, al- 

 though tried under varying conditions, I have not been able to observe 

 the generation of phosphorus bases in this process. The benzol chloride is 

 reduced to benzol, which itself is then no further changed, even by raising the 

 temperature, as the interesting researches of M. Baeyer have already proved. 



But even the action of phosphonium iodide on phenol, from which, 

 looking at the experience gathered in the methyl and ethyl series, I was 

 fairly entitled to hope that at least the tertiary and quartary compounds 

 would emerge, gave rise to changes very different from those anticipated. 

 The singular phosphorus bodies generated in this reaction claim further 

 examination. New processes, different from those hitherto followed, must 

 therefore be devised for the production of phenylphosphine. 



Exactly as in the formation of phenylphosphine, I have hitherto failed 

 in that of phosphoretted toluidine. On the other hand, the preparation 

 of a phosphorus base corresponding to benzylamine presents no difficulty. 

 Considering that benzyl chloride is easily converted into benzylamine by 

 the action of ammonia (as the researches of Cannizzaro and Limpricht 

 have shown), it could not possibly be doubted that by causing benzyl 



