254 



Especially in cyclic compounds, the presence of such double bonds 

 can be of interest, for the question of the resolvability of the molecule 

 into optically active antipodes. 



Pope, Perkin and Wallach *) prepared and studied the 



i-methyl-cydohexylidene-4-acetic acid : 



COM 



This molecule has no symmetry at all, and indeed it appeared 

 to be resolvable into optical antipodes by the aid of brucine. 



The dibromo-addition compounds preserved their activity also, 

 and the same was found for the corresponding hexanes. The @-dextro- 

 acid could be obtained in tetragonal crystals, measured by Halli- 

 mond, but these did not exhibit any trace of hemihedrism. 



A case similar to this, is that of ^.-oximino-cyclohexane-carboxylic 

 acid : 



=N OH 



which was prepared by Kay and Perkin 2 ), and which was first 

 split up, by means of morphine, by Mills and Bain 3 ). 



Somewhat different, - - because one of the carbon-atoms may 

 be concerned as asymmetrical, is the case of the fission of the acid : 



-CH 2 -C0 2 H 



1) W. J. Pope, W. H. Perkin Jr., and O. Wallach, Journ. Chem. Soc. Lon- 

 don, 95. 1789. (1909); W. J. Pope and W. H. Perkin Jr., Journ. Chem. Soc. 

 99. 1510. (1911); A. E. Everest, Chem. News, 100. 295. (1909); J. E. Marsh, 

 Proceed. Chem. Soc 27. 317. (1911); P. F. Frankland, Journ. Chem. Soc. Lon- 

 don 101. 654. (1912). 



2) F. W. Kay and W. H. Perkin Jr., Journ. Chem. Soc. 89. 1640. (1907). 



3) W. H. Mills and A. M. Bain, Journ. Chem. Soc. 97. 1866. (1910). 



