Interconversion between the separable 2,4,6-tri-tert-butylanilide rotamers was found to easily occur through formation of the lithium enolate. Protonation of the anilide enolate gave the anilide rotamer mixture of E-major. On the other hand, reactions of lithium enolate prepared from 2,4,6-tri-tert- butylpropionanilide with alkyl bromides preferentially afforded a Z-rotamer of alkylated products.
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry