Notable structural property of 2,4,6-Tri- tert -butylanilide enolates: Interconversion between the rotamers and their reactivity

Yusuke Ohnishi, Masahi Sakai, Shouta Nakao, Osamu Kitagawa

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2840-2843
Number of pages4
JournalOrganic Letters
Volume13
Issue number11
DOIs
Publication statusPublished - 2011 Jun 3

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ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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