322 



REPORT — 1900. 



and not only is this the case, but the derived formula of camphononic 

 acid is in complete accordance with the disinclination of the carbonyl 

 group to form additive complexes (compare E. 2. a. ii.). 



The Perkin-Bouveault formula is, in tliis instance also, inapplicable, 

 unless, as usual, a special assumption is made to meet the case. Thus, 

 no doubt, it might be held that an intermediate compound having the 

 formula 



.CO-CH. 



CH, 



CO.COOH 



\CMe,.CMe.COOH 



is produced which breaks up into oxalic acid and camphononic acid by 

 hydrolysis. Such an assumption, however, has nothing to recommend it. 



2. The Perkin-Bouveault Formula. 



/CMeo-CMe — CO 



/ 

 CH2 



CH, 



-CH CH., 



This formula ofifers simple explanations of the following points, for 

 which the Bredt formula appears inadequate. 



(a) The Formation of Isolauronolic Acid from Camphoric Acid in 



several Ways. 



The formation of this acid by elimination of the aZZo-carboxyl group 

 from camphoric acid is readily explained by the use of this formula : 



/CMe, . CMe . COOH 



CMe, . CMe 



CH, 



CH, 



CH,— CH . COOH 



+ 2H + CO., 



^CH,— C . COOH 



The change represents the formation of acids having the formula proved 

 by Blanc to be correct for isolauronolic acid, and of course affects both 

 asymmetric carbon atoms, thus explaining the complete disappearance of 

 optical activity during their formation. 



(b) The formation and properties of ^-campholenic acid. 



In explaining the production of a campholenonitrile from caraphor- 

 oxime, as represented by the Perkin-Bouveault formula, we are led in a 

 most simple manner to the formula, which, as was pointed out by Bou- 

 veault, is the most suitable one for )8-campliolenonitrile which can be 

 devised : 



.CMe.2-CMe.C: NOH 



, CMe.,— CMe CN 



CH, 



CH, 



CH.,— CH CH, 



CH, 



-CH., 



