

CoH 7 





H,Cf 



I 



1 

 



0H 2 



H 2 C 



1 



CH 2 



CRYSTALLINE CAMPHOR OF EUCALYPTUS OIL. 105 



inclined to believe that the constitution of these compounds is 

 similar to that of the salts of nitrogenous and other bases. This, 

 however, assumes that oxygen may behave as a quadrivalent 

 element. In favour of this hypothesis, the authors instance such 

 compounds as dimethyl ether hydrochloride, diethyl ether hydrio- 

 dide, ether peroxide, etc. 



If the oxygen atom in eudesmol be depicted as quadrivalent, 

 then by taking Briihl's formula for eucalyptol the following con- 

 stitutional formulae might be suggested, considering iso-propyl 

 present as in cymene. 



C 3 H 7 



I 



HoCT | s oflo 



HCT | ^CH 



I I 



CH ;3 CH 3 



Eudesmol. Eucalyptol. 



This would necessitate the arrangement of the fourth affinity of 

 the carbon atoms of the nucleus on the centric formula. 



As eudesmol on oxidation with nitric acid gives camphoronic 

 acid as one of its oxidation products, we may perhaps derive some 

 assistance by considering the probable formula for that acid. 



Bredt 1 from investigation of its salts considered camphoronic 



acid to be isopropyltricarballyic acid and to have the formula 



CH 3 CH-CH 3 OH 3 -CH-CH 3 



I I 

 CH 2 C CH 2 or CH CH CH 2 



III III 



COOH COOH COOH COOH COOH COOH 



thinking the first of these the more probable. 



In an important paper on the synthesis of i-camphoronic acid 

 by Perkin and Thorpe 2 it is shown that camphoronic acid has the 

 constitution of a trimethyltricarballylic acid of the formula 



1 Annalen, 1884, 226, 249 - 261. 2 Journ. Chem. Soc, 1897, 1169. 



