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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Anilides
Lithium
Structural properties
reactivity
lithium
Protonation
Bromides
bromides
products
2,4,6-tri-tert-butylanilide

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Notable structural property of 2,4,6-Tri- tert -butylanilide enolates : Interconversion between the rotamers and their reactivity. / Ohnishi, Yusuke; Sakai, Masahi; Nakao, Shouta; Kitagawa, Osamu.

In: Organic Letters, Vol. 13, No. 11, 03.06.2011, p. 2840-2843.

Research output: Contribution to journalArticle

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