176 



of succinic acid (m. p. 182°). When fractionated the oil yielded succinic 

 anhydride as well as caryophyllenic acid. 



The authors conceive the diketo acid to be a derivative of lim.- 

 caryophyllene, possibly according to the following reaction: — 



Lim.-Caryophyllene -j- Ozone 



CCH 3 



CH 2 



H 2 C 







CH < 





H 3 C« C • CH3 





HC 



\ 



CO 



\ 



COOH CH 3 



(CHO) 



Diketo acid, 



or Diketo aldehyde. 



CO 



+ HN0 3 



H 2 C 



Caryophyllenic acid + 



HOOC 



COOH 



Succinic acid. 



In the course of the distillation of the acid oxidation products the first 

 runnings consisted of an acid C 8 Hi 4 2 , b. p. 120 to 128° (9 mm.), of which 

 the amide had m. p. 96°. 



The ketone Ci Hi 8 O referred to above, when oxidised with bromine 

 solution, yielded an acid C 9 Hi 6 2 (b. p. 131 to 133° at 13,5 mm.; m. p. of 

 the amide 114°). Oxidation with nitric acid resulted in an acid C 8 Hi 4 02 

 (b. p. 119 to 122° at 12 mm.; m. p. of the amide 115 to 116°). The authors 

 regard the ketone Ci Hi 8 O as a secondary decomposition product of the 

 ozonisation, and as having the following genesis: — 



Terp.-Caryophyllene 

 HNO3 



CH-CHs 



H 2 C 



CH-CH, 



4 



C(CH 3 ) 2 



COOH hc 1 ; 



CH 2 CHs 



Ketone Ci H 18 O. 



CH 2 



Acid C,H l6 2 . 



COOH 



Acid C 8 H!4 02. 



