190 Miss Thomas and Mr Jones, A Series of Optically Active 



A Series of Optically Active Nitrogen Compounds containing 

 the Allyl Group. By Miss M. B. Thomas, Girton College, and 

 H. O. Jones, M.A., Clare College. 



[Received 27 November 1905.] 



In an earlier communication {Proc. 1904, xiii. 33) an account 

 was given of the preparation of some salts of substituted quater- 

 nary ammonium bases and their resolution into their optically 

 active constituents, which was undertaken with the object of 

 determining whether the relation between rotatory power and 

 constitution would be more evident in the case of ions' than 

 it is in complete molecules. The salts then examined were those 

 in which three of the hydrogen substituting groups were phenyl, 

 methyl, and benzyl, the fourth atom of hydrogen being successively 

 replaced by the isopropyl and isoamyl radicals. A comparison of 

 the molecular rotatory powers of the basic ions with those obtained 

 for the corresponding ethyl compound shows that a maximum is 

 reached when the isopropyl group is substituted, the rotatory 

 power of the ion containing this radical being greater than that 

 of the ions containing the ethyl or isoamyl radicals. 



A more complete homologous series of five compounds has 

 been prepared, each of which contains the radicals phenyl, methyl, 

 and allyl, while the fourth ammonium hydrogen atom is replaced 

 successively by the ethyl, propyl, isopropyl, isobutyl, and isoamyl 

 radicals. 



The compounds have been resolved into their optically active 

 components by the method of Pope and Peachey. The d.-camphor- 

 sulphonate or d.-brom.-camphor-sulphonate of the base is made by 

 the interaction of the quaternary substituted iodide with the 

 silver salt of the acid in acetone or other suitable solvent, and 

 the resulting salt is recrystallised until a constant rotatory power 

 is obtained. A tabulated list of the results obtained is given 

 below. The values of the molecular rotatory power are for 

 dilute aqueous solutions at 15° C. ; the values for the ions all 

 decrease slightly with increasing temperature. 



