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Herein, we report a unique structural property of 2,4,6‐tri‐tert‐butylanilide, which can be separated into its amide rotamers at room temperature. Interconversion between the rotamers of anilide enolates occurs readily at room temperature and their reaction with electrophiles gives mixtures of the rotamers in a ratio that depends on the reactivity of the corresponding electrophile. That is, the reaction...
Z-Rotamers of several 2,4,6-tri-tert-butylanilides slowly isomerize at rt in CDCl 3 to E-rotamers, yielding equilibrium mixtures of Z- and E-rotamers after standing for 1 week. The equilibrium ratios between the anilide rotamers in the solution depend strongly on the bulkiness of the acyl substituents as well as the formation of intramolecular hydrogen bond. Heating equilibrium mixtures in...
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