— 137 — 



The action of aluminium chloride and acetyl chloride on isolaurolene 

 produces a ketone, and reduction with sodium and alcohol from the 

 latter the secondary alcohol 



CH, CH Q 



CH 2 



CH, 



CH-CH 3 



CH — CH(OH) — CH 3 



which on oxidation with nitric acid yields dihydroisolauronolic acid, 

 and by brominating the hydrogen atom in the a-position, and loss 

 of hydrobromic acid, yields isolauronolic acid. 



As to the conditions regarding the dynamic isomerism in camphor 

 derivatives, see under Physical notes, p. 105. 



Fenchone. As already mentioned by us in our last Report 1 ), 

 various reactions of fenchone and camphenilone had induced 

 F. W. Semmler to draw up for the former a formula which differs 

 from the otherwise generally accepted formula of Walla ch. From 

 Semmler's formula, fenchone appears as a methylated camphenilone, 

 whilst according to Wallach camphor and fenchone differ solely in 

 the position of the methyl groups. Semmler 2 ) sees in the products 

 of decomposition of fenchone fresh evidence for his view. A reagent 

 which has a closer relationship to the CO-group, and consequently 

 splits up the molecule at the keto- group, was found by his recent 

 researches in sodium amide. Cyclic ketones which, like fenchone, 

 possess next the keto-group a dimethylated carbon atom, suffer by the 

 action of sodium amide a ring-disruption, with formation of the sodium 

 amide of the corresponding acid: — 



/CH 9 C v /CH Q 



c c 



| X CH 3 _> | X CH 8 



CO H 



/ CO-NHNa 



C / 



C 



Dihydrofencholenic acid amide, C 10 H 19 ON, is formed by the action 

 of molecular quantities sodium amide on fenchone in benzene solution 



*) Chem.-Ztg. 29 (1905), 1313; Report April 1906, 124. 

 2 ) Berl. Berichte 39 (1906), 2577. 



