318 REPORT— 1900. 



of which the second, as has already been stated, has nothing further in 

 its favour, and it does not appear possible to explain by its use the 

 properties and constitution of many important products obtained by 

 degrading the camphor molecule in the various ways detailed in E. 



It is quite clear, therefore, that in the light of our present knowledge 

 only two formulre for camphor can be regarded as in the slightest degree 

 probable, namely, the Bredt and the Perkin-Bouveault formulae ; and 

 although it might at first sight appear an easy matter to decide between 

 two formulte so different in configuration, each still finds support in 

 apparently incontrovertible evidence. A list of the facts to which each 

 formula appears capable of ready application may be dealt with in turn, 

 only those points being taken which appear to be of use in coming to a 

 decision as to the relative value of the two formulae. 



(a) The Constitution of a-CamphoIenic Acid and its Oxidation Products. 



The formation of a nitrite having the highly probable constitution 

 assigned to a-campholenonitrite by Tiemann is readily explained as follows 

 , (compare E. 4.) 



CH /CH 



/ I \ / 



CHo CHo CHo 



CH, 



CN 



2 



I CMeo I - H,0= I CMe, 



CH2 I "C:NOH " CH 



^CMe CMe 



(b) The Non-fonnation of an Anhydride from Itomocamphoric Acid. 



In accordance with Bredt's formula, homocamphoric acid must have 

 the formula (compare B. 2. b. and E. 3.) 



CH 







CH2 



CH.CH2.COOH 



CMe, 



^ CMe.COOH 



Homocamphoric acid has been shown to be incapable of yielding an 

 anhydride,' a fact with which the above formula is in accordance, as it 



' Bredt, Ann., 289, 6. 



