518 REPORT—1904. 
thylenedipiperidide, C,H,,N .CH,.CH,.CH,.NC,H,,, the author bas obtained 
two stereoisomeric compounds having the constitution, 
, Br Br 
GS ie bias 
peach NOH, CH, .CH,7 Soup gr 
which he was unable to resolve into optically active components by the aid of 
Pope’s method with d-camphorsulphonice acid. Both compounds would therefore 
seem to possess symmetrical configurations, and this is only possible if the above 
conception of the arrangement of the valency directions of the pentavalent 
nitrogen atom is correct. 
Since the attempts at resolution were carried out in aqueous solution and as 
possibly the d-camphorsulphonic acid is not capable of effecting an easy separation 
of the stereoisomerides, the two ethylenetrimethylenedipiperidide dibromides were 
caused to react with silver d-bromocamphorsulphonate in absolute methyl alcoholic 
solution. Both gave highly crystalline ethylenetrimethylenedipiperidide d-bromo- 
camphorsulphonates which were separated by crystallisation into four and three 
fractions respectively, the fractions being then converted into the difficultly 
soluble iodide by precipitation with potassium iodide, The samples of iodide 
from the first and last fractions were then immediately examined polarimetrically, 
but were found to be optically inactive. 
The author finds in these results a confirmation of his previously expressed 
views on the configuration of ammonium compounds, and notes also that this 
view possesses the greatest probability on grounds of a mechanico-chemical nature. 
6. Zhe Asymmetric Nitrogen Atom. By Professor E, WEDEKIND. 
In 1899 I succeeded in preparing isomeric series of salts of phenylmethyl- 
allylbenzylammoniumhydroxide by different methods ; since then many attempts 
have been made to find analogous cases of isomerism among other asymmetric 
ammonium salts, and so to explain the nature of this peculiar phenomenon. I 
have already published the results of numerous experiments made with cyclic 
quaternary salts of tetrahydroquinoline and isoquinoline, and with methylethyl- 
phenylallylammoniumhydroxide, and now describe the results of experiments 
carried out with the toluidines, to see if these bases behave like aniline. 
The asymmetric salts of para-toluidine can be made by three methods. In 
spite of analogous constitution, they behave very differently from the corresponding 
compounds in the aniline series. Firstly, the iodides 
(CH,.C,H,) (C,H) (C,H,) (CH,) N.L 
prepared by three different methods, were at once obtained crystalline, and showed 
chemical and crystallographical identity. The iodide and bromide are not 
isomorphous; the crystals of the former are rhombic, of the latter monoclinic. 
Still more remarkable was the difference in the case of the homologous benzyl 
salt (C,H,*CH,) (C,H,) (C,H,) (CH,) N.I. Identical salts were obtained by all 
three methods. On the other hand, there is here a case of dimorphism; the 
crystals are triclinic, but show different angles. One form crystallises from 
alcohol, the other from water. The iodide and bromide, however, are not isomor- 
phous; and the crystals of the latter show hemihedral faces. Different relations 
were observed in the ortho-toluidine series. The tertiary bases showed but little 
tendency to combine with the alkyliodides (this is due to the sterochemical 
hindrance of the methyl] group in the ortho-position). The salts obtained with 
benzyl and allyliodide were amorphous. By the use of methyl iodide crystals were 
obtained ; the quantity, however, was too small to allow of chemical and crystallo- 
graphical examination. The properties of the latter salt seem to show that there 
is here a second case of the new nitrogen isomerisin. 
Since the preparation of optically active nitrogen compounds the question has 
