536 



Mr. C. G. Williams. 



[Mar. 17 y 



near the centre, and as the polarised ellipses are at an angle with the 

 molecules of the central portions of the wire, its polarisation reacts 

 upon them, producing the comparatively strong electric currents I 

 have described. 



III. : t "On the Action of Sodium upon Chinoline." By C. 

 Greville Williams, F.K.S. Received March 8, 1881. 



In 1867 I made some experiments on the action of sodium upon 

 chinoline and lepidine, and found that a siibstance was produced which 

 dyed silk a beautiful but fugitive orange colour. I announced this 

 fact in a paper " On the Higher Homologues of Chinoline."* I made 

 analyses of the products at the time, but the difficulties in the way of 

 preparing them pure were so great, and the time at my disposal was so 

 limited, that I did not make public any quantitative results until 

 March, 1878, when I published a short note "On the Action of Sodium 

 on Chinoline and Lepidine. "f In that paper I gave the results of an 

 analysis of a product from chinoline, which agreed with the formula 

 C 18 H 14 N 2 .HC1, which is obviously that of the hydrochlorate of dichino- 

 line. I also gave an analysis of the nitrate of dilepidine, which 

 agrees almost perfectly with the theoretical values ; but I did not 

 enter into the details of the modes of preparation. In the course of 

 my investigation of /3-lutidine, it was natural that I should study the 

 action of sodium upon it, but I met with so many and unexpected 

 difficulties that I determined to prepare myself for a new attack upon 

 the subject by a fresh investigation of the action of sodium upon 

 chinoline. As I find that other observers are working upon chinoline, 

 /3-lutidine, and /3-collidine, J I have thought it desirable to bring before 

 the Society the results obtained, although the investigation is still 

 proceeding. 



Action of Sodium upon Chinoline. 



The action of sodium on chinoline is exceedingly remarkable, not 

 merely because it polymerises the base, for a similar result, as is well 

 known, takes place with picoline, but because the products have pro- 

 perties which are, I think, different from any yet observed among 

 organic substances. For a yellow oil like dichinoline to yield a true 

 although fugitive dye, in the form of a brilliantly red crystalline 



* " Laboratory," May, 1867, p. 109. 

 f " Chemical News," March 1, 1878. 



% Richard, " Bull. Soc.Chim.," [2] xxxii, 486— 489 ; Boutlerow and Wischnegrad- 

 sky, loc. cit., ~No. 9, June 5, 1880 ; Oechsner de Coninck, " Bull. Soc. Chim.," Nos. 4 

 and 5, p. 210, September 5, 1880. The latter chemist has repeated several of my older 

 experiments, evidently under the impression that they had not been made before. 



