466 Mr Jones, Note on Compounds containing an Asymmetric 



Note on Compounds containing an Asymmetric Nitrogen and 

 an Asymmetric Carbon Atom. By H. O. Jones, M.A., Clare 

 College. 



[Received 26 April 1904.] 



The investigation of compounds containing both an asymmetric 

 nitrogen and an asymmetric carbon atom was undertaken in the 

 hope that the phenomena exhibited by them might throw further 

 light on the problem of the isomerism of quinquevalent nitrogen 

 compounds. 



It was to be expected, if the analogy between the behaviour 

 of asymmetric carbon and nitrogen atoms held in this case, that 

 when a tertiary amine in which one of the groups contained an 

 asymmetric carbon atom combined with an alkyl iodide so as 

 to produce a compound containing an asymmetric nitrogen atom, 

 unequal quantities of the two possible isomerides would be 

 produced, which, not being optical antimers, might be separated 

 by ordinary processes. These compounds might be represented 

 thus: 



b b 



R'_N — R" and R'— N — R" 



/\ /\ 



R '" X X R'" 



and would bear to one another a relation similar to that of the 

 a and /3 glucoheptonic acids or the two a/3 dihydroxybutyric 

 acids. This expectation has been realised, and another analogy 

 between the behaviour of asymmetric nitrogen and carbon com- 

 pounds established. 



The tertiary amine used was methyl Z-amyl aniline, which 

 was prepared as pure as possible, and found to be dextro- 

 rotatory oy 5 = 10-8°. 



In order to ascertain, if possible, what kind of rotatory power 

 would be given to the salts by the active amyl group alone, the 

 union with methyl iodide was studied. The union to form a 

 crystalline salt takes place readily, but the salt examined in 7 per 

 cent, alcoholic solution had no observable rotatory power. The 

 effect of the carbon atom is therefore extremely small. The fact 

 that the compound thus produced is inactive affords further 

 evidence in support of the author's conclusion that compounds 

 of the type N.R / R"R/" 2 X could not show optical activity {Trans. 

 Chem. Soc. 1903, 83, 1420). 



