182 REPORT—1904. 
(iii) Compounds of the type Nabe X. 
Messrs. Schryver and Collie! prepared the chloroplatinate of methyl- 
diethyl-isoamylammonium hydroxide from the iodides formed in the three 
possible ways, and found that when the processes were carried out in the 
cold, two crystalline modifications were obtained, an oblique and a pris- 
matic, the former of which was unstable and readily passed into the 
latter. This difference might easily be due to dimorphism, as in the case 
of the compounds of the type Na,6 X. 
The writer’ investigated the formation in two different ways of a 
number of compounds with two identical radicals, and found that even 
when the reaction was carried out in the cold, the products obtained were 
in all cases the same. In a few instances the crude compounds differed 
to a slight extent, and one might even be gummy while the other was 
deposited in a crystalline state ; these differences always disappeared 
when the substances separated from solutions. The d-camphor sulphonates 
prepared from both products were the same. 
All attempts to get isomeric piperidinium salts have also been unsuc- 
cessful. Thus Menschutkin* found that ethyl-allyl-piperidinium iodide 
produced in the two possible ways was the same and so also was the 
chloroplatinate. Miss de Brereton Evans‘ obtained only one form of 
ethyl-propyl-piperidinium iodide, the crystals of which, however, showed 
enantiomorphism, and Wedekind’ obtained only one form of benzyl- 
piperidinium iodide, methyl- and ethyl-acetates, and the corresponding 
bromides 
Aschan ® has investigated dipiperidinium derivatives, and though he 
obtained only one form of N.N. ethylene dipiperidinium dimethy] diiodide 
and the corresponding dibenzy] dichloride, found that two isomerides of 
ethylene-propylene dipiperidinium dibromide and of ethylene-trimethylene 
dipiperidinium dibromide and diiodide’ seem to exist. 
The first of these compounds contains an asymmetric carbon atom : 
OH. CH) +1: CHs—CHs;. CH,..CH, 
oon Pine Tis yee 
CH, CH, _C H——CH,| CH, CH, 
Mae 
Br CH, Br 
whereas the others do not: 
CH, CH, CH, 
CH, CH, CH, 
ares “e 
be Retiee eA Now 
OBS ¥ LY as 
CH, CH, | CH,—CH,—CH,| CH, CH, 
Br Br 
! Proc. Chem. Soc., 1891, vii. 39. 
2 Proce. Camb. Phil. Soe., 1901, 11, 111; Trans. Chem. Soc., 1903, 88, 1400. 
® Zeit. phys. Chem., 1895, 17, 228; Ber., 1895, 28, 404. 
4 Trans. Chem. Soc., 1897, 71, 522. ; 5 Stereochemie, 58. 
© Bev., 1899, 82, 988; Zeit. phys. Chem., 1908, 46, 304. 7 Loe, cit., 306. 
