ON THE CONSTITUTION OK CAMPHOR. 



321 



— CH2 — group in a hydrocarbon ring may be converted into — CH(OH) — • 

 or — CO — or others equally improbable : 



CH, CH., CH . COOH 



/I 

 ^ CMe., 



CMeo 



CMe(COOH) . CH . COOH 



CMe. COOH + COOH .COOH. 



(g) The Foi-mation of Gam'phorphorone (^compare E. 5.). 



The formation of a ketone having the constitution of camphor- 

 phorone from calcium camphorate receives instant explanation by means 

 of Bredt's formula, as follows : 



.C 



CH., „// \ 

 I " CMeo 

 CH., 



CH2 



I 

 CH2 



,CH.C0.0 



CMe.3 



;Ca 



CO + CaCC), 



CMe. CO. O 



CM 



whilst if the Perkin-Bouveault formula is used the change must be 

 represented as the result of the following complicated series of reactions : ^ 



,CMe., . CMe. CO 



CH„ 



-CHo— CH 



O 



/CMe., CHMe.CO. 



CO . O 



( 

 / 



Ca 



CH 



CH, CH- 



CMe2 CO.CHMe 



\ 



CH, 



-CH, 



a necessity which leaves the probabilities greatly in favour of the first 

 depicted. 



(h) The Formation of Camphononic Acid and Oxalic Acid from Dihydrohomo- 

 Camphoric Add (compare E. 3.). 



As has already been mentioned {loc. cit.) this change appeals capable 

 of only two simple explanations, one of those being the assumption that 

 dihydrohomocamphoric acid has the formula which would be attributed 

 to it were Bredt's formula the correct one, namely 



.C=CH.COOH 



CH, 



CH, 



CMe., 



1900. 



^CMe.COOH 



' Compare Bouveault, JivlL iS'oc. Chim. [iii.], 19, 4f)2. 



