184 REPORT—1904. 
differed in a similar way to the a and # iodides. Hantzsch and Horn ! 
prepared the a and / iodides and made experiments to exclude the possi- 
bility of structural differences. Both iodides react as unsaturated bodies 
toward alkaline permanganate, and on oxidation give formic acid,which 
facts show that both are allyl compounds. 
The writer has compared the properties of the 4 compound with those 
of phenyl-methy1l-benzy]-propy] and zsopropyl ammonium iodides, and found 
that it differs from both in melting-point and crystalline form, though in the 
latter particular it has a slight resemblance to the zsopropyl compound. 
No other case of a similar kind has been found, though Wedekind was 
deceived by abnormal reactions into thinking that there were isomerides 
of some other compounds. Thus the addition of allyl bromide to benzyl 
isobutyl-N-methyl-acetate and of methyl-brom-acetate to benzyl-allyl- 
isobutylamine gave rise to different products, the latter of which was 
subsequently found to be a mixture. 
Methyl-allyl-tetrahydroquinolinium iodide? prepared in two ways was 
the same, and so with ethyl-benzyl-zsotetrahydroquinolinium iodide.* 
The tetrahydroquinolinium derivatives produced by the addition of 
methyl] iodide and of methyl- and ethyl-iodo-acetates to the corresponding 
tertiary tetrahydroquinoline compounds and which were at first thought 
to be isomeric * were afterwards ° found not to have the same composition. 
Methyl] tetrahydroquinolinium N-methyl- and ethyl-acetate iodides were 
produced by the first method, but the second gave a mixture of these with 
kairolin hydriodide. 
similar tetrahydroisoquinoline compound was obtained in one form 
only. 
Wedekind has also studied the formation of compounds in which two 
asymmetric nitrogen atoms are present.’ Ethylene dikairolinium di- 
iodide was prepared in two ways and found to be the same; ethylene 
ditetrahydroquinolinium di-ethyl-acetate di-iodide, however, appears to be 
different when prepared in the two possible ways ; the specimen formed by 
the addition of iodo-acetic ester melts at 164-165° C., whereas that formed 
by the addition of ethylene di-iodide melts at 50° C., with elimination of 
one molecule of iodo-acetic ester. The analyses of these compounds are, 
however, insufficient to prove identity, and it is possible that one of them 
is a mixture. 
Wedekind examined the stable compound to ascertain if it was homo- 
geneous, and decided that it was. Hence, the analogy between asymme- 
tric nitrogen and carbon does not seem to hold here—namely, that, when 
two asymmetric atoms are produced, all four possible compounds should 
also be produced and combine in pairs to give externally compensated 
compounds separable by crystallisation. 
(v) Optical Activity of Substituted Ammonium Compounds. 
It was expected from analogy with carbon compounds that quinque- 
valent nitrogen compounds, N ab cd X, would exist in optically active forms, 
and repeated attempts were made to prepare such compounds before 
definite success was attained. 
Le Bel® submitted dilute aqueous solution of various salts of the type, 
1 Ber., 1900, 35, 883. 2 Stereochemie, 75; loc. cit., 63. 
8 Ber., 1901, 34, 3986 4 Stereochemie, 66. 5 Ber., 1902, 35, 178. 
5 Ber., 1903, 36, 1158. 7 Ber., 1903, 36, 1165, 3796.8 ® Compt. rend., 112, 724. 
