520 REPORT—1904. 
The single fractions showed the same specific rotatory power and a molecular 
rotation of + 105°to 104°. The di-d-brom-camphorsulphonate crystallises remark- 
ably well, and seems to offer a better chance of resolution. The acetic ester of 
kairolinium d-camphorsulphonate ([a]>=11'7°) has not. been obtained in active 
forms either by Jones or myself. 
The problem of examining the so-called inactive isomers of asymmetric nitrogen 
offers great difficulties. Anyone who has examined so great aseries of asymmetric 
systems for isomers without success as I have, will understand me when I call 
the single case of isomerism in the series of benzylallylphenylmethylammonium 
salts (which I discovered several years ago) ‘remarkable,’ and to a certain extent 
a ‘puzzle.’ Kipping and Aschan have both taken exception to this expression. 
I think, however, that everyone will agree with me that the extraordinary rarity 
of such isomers—predicted by most theories—is most striking, especially as in the 
observed case the isomers possess about equal stability. Since then I have found 
a new case in the series of asymmetric ortho-tolyl-ammonium salts, but on account 
of experimental difficulties 1 have not been able to establish it with absolute 
certainty. Since among the homologues of the asymmetric aniline salt, with this 
exception, no isomers have been found, I have commenced experimenting with the 
asymmetric phenetidine and anisidine bases.!_ Paraphenetylbenzylallylmethylam- 
monium iodide (and the corresponding d-camphorsulphonate) are beautifully 
crystallised salts when made by the combination of allyl or benzyl iodide with 
the corresponding tertiary bases. The third method—addition of methyl iodide to 
benzylallyl-p-phenetidine—leads to an amorphous salt, Experiments are already 
in progress to prove if this is really a case of isomerism. 
O. Aschan has recently discovered a new case of isomerism in the series of the 
diacid ammonium salts which differ in solubility. At the time of his publication 
I was working on the ethylene bases of the tetrahydrozsoquinoline series. I 
therefore tried whether the above-named bases, which in contradistinction to the 
piperidine derivatives are quite unsymmetrical, possess analogous powers of 
reaction. The reaction between trimethylene bromide and ethylene di-tetrahydro- 
erengnee takes place almost quantitatively at 100° C. The equation pro- 
ably is :— 
CH, H,C 
OH, H,C 
N—CH,—CH,—N 
CH, H,C 
+ Br. CH, . CH,. CH, Br 
CH, H,C 
CH, H,C 
u ee 7 OCH 
N- SN 
se. \ oth otte Jy OH, 
ff 
Br BY 
According to this, the salt, which is rather easily soluble in water, would 
contain a seven-atom heterocyclicsystem. The prospects of successfully preparing 
this system by the second method are not good, since, according to my experience, 
1 T intend to try to resolve the fatty asymmetric base of Le Bel, N(CH;)(C,H;) 
C,H,)(@.C,H,)OH by the new method. 
