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W h i t m a n , J. Am. Chem. Soc. 76, 1899 (1954). R. Wegler and G. P i e p e r , Chem. Ber. 83, 1 (1950). D. G. Hill and G. B. K i s t i a k o w s k y , J. Am. Chem. Soc. 52, 892 (1930). S. E. Voltz, J. Phys. Chem. 6 1 , 756 (1957). A. J. H u b e r t , J. Chem. Soc. [C] 2149 (1967). F. W. B e r g s t r o m and J. F. C a r s o n , J. Am. Chem. Soc. 63, 2934 (1941). L. H . Slaugh, Tetrahedron 22, 1741 (1966). O . Fischer and E. H e p p , Chem. Ber. 26, 2231 (1893). A. W a n s c h e i d t , Chem.

2) and (3) shows that the same mesomeric anion results from either 3 or 6, which can be thought of as involving t w o e x t r e m e forms, one a primary anion and the other a secondary anion: The mesomeric anion p r o d u c e d in E q . (4) can also be considered to have two e x t r e m e forms, one a secondary anion and the other a tertiary anion [36]: 40 2. Isomerization of Olefins This seems to be a rather clear illustration of the lower stability of tertiary carbanions as compared to secondary or primary carbanions and also supports the proposed anionic mechanism for olefin isomerization [20].

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