SYNTHESIS AND OXIDATION OF TERTIARY 
HYDROCARBONS. 
"By P. A. LEVENE anv L.. H. CRETCHER, Jn. 
- (From the Laboratories of The Rockefeller Institute for Medical Research.) 
(Received for publication, January 31, 1918.) 
The present investigation was evolved from the previous work 
on the structure of branched chain fatty acids. Levene and 
Allen! have called attention to the lack of a convenient method 
for determining the location of the tertiary carbon atom in the 
‘branched chain fatty acids. An attempt was made to solve the 
problem by the oxidation of the fatty acids themselves in the 
hope that the tertiary carbon atom, as the one most susceptible to 
oxidation, might prove to be the point of disruption of the carbon 
chain. It is still possible that the solution of the problem may 
be reached by this mode of attack. Experience has shown, how- 
ever, that the oxidation of any fatty acid takes place at more 
than one point of its carbon chain. Because of this the products 
of oxidation are numerous and it is not always an easy task to 
formulate the structure of the original molecule on the basis of 
many fragments. Hence it was thought that an advantage 
might be gained if prior to oxidation the molecule of the acid 
could be so transformed as to possess fewer points susceptible to 
the action of oxidizing agents. It was natural to think in this 
connection of the hydrocarbons, since every fatty acid is readily 
‘convertible into the corresponding hydrocarbon. 
Can tertiary hydrocarbons be oxidizéd by a permanganate 
solution, or by some other ‘oxidizing agent? The literature on 
the subject is very meager. In 1901, Zelinsky and Zelikow? 
made the observation that 3-methylpentane is readily oxidized 
by means of potassium permanganate. Prior to that observa- 
1 Levene, P.'A., ‘and Allen, C:'‘H., J. Biol. Chem., 1916, xxvii, 433. 
2 Zelinsky, N., and Zelikow, J., Ber. chem. Ges., 1901, xxxiv, 2865. 
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