io Robinson, The Conjugation of Partial Valencies 



CH 



Camp holy tic acid -> P-C amp holy tic acid (isolauronolic 



acid). 



COOH 



Hi 



CH COOH 



CH 



% 



\ 



( 



/ 



C Me 



CMe 



d.l H 2 S0 4 



ch; 



ch< 



H(x) N c ^Me 



(Woh 



Me 



Me(R'J 



COOH 



l 



CH 2 iS^v 



I 1} CMe 



COOH 



i 



<? H 2 H % 



CH 2 OH 



CMe 



C- 



Me 



....'Me 



CH, 



OH 



/ 



C-^Me 

 Me 



i-Methyl-i-a-hydroxyethylcycfopentane -» 1.2-Dimethyl-A 

 cyc/ohexene. (H. Meerwein, Annalen, 191 8, 417, 255.) 



CH 



CH 2 - 



CH ? C — CH 2 — H(x) 



\ /\ 



CH 2 CHMe-OH(y) 

 (R') I 



t 



«a ^~C Me 

 CH 2 „ 



CH 2 CMe 



I 



(in) 



CH 2 



*, 



CH, 



CH. 



CHp-CH- 

 Me 



:CH 2 v 

 .QH" 



"V-H 



-CH 2 



I 



C=CH 2 ,H 

 CH 2 J HO 



NH-CHMe 



(I) 



