178 Mr Buckney,An optically active tetrahydroquinoline compound. 
half-an-hour on the water bath, when all the iodide was com- 
pletely decomposed. After filtering and evaporating off the 
acetone, the gummy residue readily became crystalline when left 
in a desiccator. The crystals were readily soluble in acetone and 
ethyl acetate and sparingly soluble in toluene. 
It was recrystallised repeatedly from a mixture of ethyl acetate 
and a little toluene, when it was noticed that two kinds of crystals 
separated out, small colourless transparent crystals sparingly soluble 
in ethyl acetate which when recrystallised several times over from 
ethyl acetate melted at 164° C., and silky needles readily soluble 
in ethyl acetate which when pure melted at 153 - 5° C. 
The less soluble salt was readily separated mechanically from 
the other and was repeatedly recrystallised from ethyl acetate, and 
its rotatory power in aqueous solution was determined. 
After three recrystallisations 
0T598 in 16'028 solution in a 220 mm. tube gave a z , = 0 - 98°, 
whence [a] z , = 49T° and [M] D = 245°. 
After two further recrystallisations 
0T610 in 17T23 solution in a 220 mm. tube gave a fl = 0'81°, 
whence [«]/> = 39T6 0 and [M] D = 195°. 
This is evidently the 1-base d-acid salt and the value of [M] D 
yCB, 
for the basic ion C 9 Hi 0 : Ny is about — 75°. 
x c 3 h 5 
The more soluble crystals were then examined, and recrystal- 
lised repeatedly from a mixture of ethyl acetate and toluene. The 
rotatory power was determined in aqueous solution. 
0T678 in 17’457 of solution in a 220 mm. tube gave a n = T45°, 
whence \a\ D = 68'6° and [M] n = 342°. 
This is therefore the d-base d-acid salt, and the value of \_M] D 
for the basic ion is +72°, which agrees well with the value ob- 
tained for the laevo-rotatory ion. 
Analysis of both salts shows that they have the same composi- 
tion corresponding to C 23 H 32 NBr 2 S0 4 . 
Unfortunately the iodide is fairly soluble in water and could not 
be recovered from the d-bromocamphorsulphonate. There is no 
doubt however that the salts obtained are d-allyl kairolinium d- 
bromocamphorsulphonate and 1-allyl kairolinium d-bromocamphor- 
sulphonate, which constitutes the first case of an optically active 
compound in which the activity is due to a nitrogen atom in 
a ring. 
This work was undertaken at the suggestion of Mr H. O. Jones, 
to whom the author takes this opportunity of expressing his 
gratitude for his advice. 
