Mr BucJcney, An optically active tetrahydroquinoline compound. 177 
An optically active tetrahydroquinoline compound. By F. 
Buckney, B.A., Sidney Sussex College. (Communicated by Mi’ 
H. O. Jones.) 
{Read 11 March 1907.] 
A large number of optically active compounds of quinquevalent 
nitrogen of the ammonium type, NR' R" R"' R iv , have been ob- 
tained but at the present time there is no well established case of 
optical activity due to a quinquevalent nitrogen atom in a cyclic 
nitrogen compound. The ethylene dikairolinium salts described 
by Wedekind (Ber. 1905, xxxviii. 1842) show anomalies which have 
as yet received no explanation. The study of these cyclic com- 
pounds becomes a matter of some importance on account of their 
bearing on the stereochemistry of the nitrogen atom. 
Quinquevalent compounds of nitrogen derived from 
picoline, from quinoline, and from tetrahydroquinoline 
H 2 
N N NH 
(when the two alkyl groups are different) contain no plane of 
symmetry and should, according to modern views, give rise to 
optically active isomerides. 
A picolinium derivative and three tetrahydroquinolinium 
derivatives have been examined by H. O. Jones {Trans. Ghem. 
Soc., 1903, lxxxiii.), other tetrahydroquinoline and several quinoline 
compounds have been examined by the author. Up to the present 
only one of these compounds has been successfully resolved into 
the two optically active forms. In this case the two salts 1-base 
d-acid and d-base d-acid have been isolated. 
Experimental. 
Allyl kairolinium iodide was prepared by 
mixing molecular quantities of methyl tetra- 
hydroquinoline (kairoline) and allyl iodide in 
the cold. Heat was evolved and the iodide 
gradually crystallised out. It was pressed 
out on a porous plate and recrystallised from 
alcohol, and finally from ethyl acetate, sepa- 
rating as small yellow prismatic crystals melt- 
ing at 130° C. 
CH 2 
CHo 
CH 2 
N— I 
Allyl kairolinium d-bromocamphorsulphonate was prepared by 
mixing together molecular quantities of the iodide and silver 
d-bromocamphorsulphonate with acetone and heating for about 
