II. CHEMISTRY 



193 



CO — , 



I 



IIO-C-II 



I 



( — OC— II 



I 



II-CO — 



I 



H— C— OH 



-CO 



NaOMc 



XXXIV 



CO— 1 



I 



HO— C 



II 



II— c 



I 



H— CO 



I 

 H— C— OH 



I 

 COOII 



XXXV 



co- 



H— C— OH 



I 

 I— OC— H 



I 

 H— CO 



I 

 H— C— OH 



I 

 CO 



XXXVII 



CO— 1 



I 



HO— C 



II 



H— C 



I 



H— CO- 



I 



HO-C— H 

 I 

 COOH 



XXXVI 



CO — 



I 



H— C— OH 



I 

 r— OC— H 



I 

 H— C— OH 



I 

 H— CO 



I 

 CO 



XXXVIII 



CO 



I 



H— C— OH 

 I 

 HO— C— H 

 I 



H— CO 



I 

 HO— C— H 

 I 

 COOCH, 



XXXIX 



COOCHj 



H— C— OH 



I 

 f— OC— H 



H— C— OH 



H— C— OH 



I 

 CO 



XL 



and in which the unsaturation has proceeded one step further beyond the 

 expected product, XLII to XLIII." 



COOMe 

 I 



CO 

 I 

 MeO— C— H 

 I 

 H— C— OMe 



I 

 H— C— OH 

 I 

 CHjOMe 



XLI 



KaOMc 



CO 



HO— C 



II 



MeO— C 



I 



H— C— OMe 



I 



H— CO 



I 

 CH.OMe 



XLII 



CO — I 



I 



HO— C 



II 

 MeO— C 

 I 

 H— C 

 II 

 CO—" 



I 



CH.OMt 

 XLIII 



" W. N. Haworth, E. L. Hirst, and J. K. N. Jones, J. Chem. Soc. 1938, 710. 



