Base-catalyzed 1-3 Prototropic Isomerization of Cycloheptatrienes

K Takahashi, H Yamamoto, T Nozoe

Index: Takahashi,K. et al. Bulletin of the Chemical Society of Japan, 1970 , vol. 43, p. 200 - 207

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Citation Number: 16

Abstract

The base-catalyzed proton migration (from the 7-to 2-position) and proton exchange (at the 7-position) of cycloheptatrienes carrying an electron-withdrawing group were studied in a medium of aqueous sodium hydroxide or alcoholic potassium hydroxide. The order of the effect of the various substituents upon the relative rates is approximately: CN> CONH 2> COO−, Ph. The base-catalyzed prototropic isomerization proceeds through: i) the ...