Reaction of benzoic esters with organolithium and -magnesium reagents. dichotomy between nucleophilic aromatic substitution and conjugate Addition

Tetsutaro Hattori, Nobuyukl Koike, Takashi Satoh, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

Abstract

The reactions of 2,6-di-tert-butyl-4-methoxyphenyl 2-methoxybenzoate 1a with several organolithium and -magnesium reagents are found to give the methoxy-substitution products 2 and/or the conjugate addition products to the benzoate ring (3 and 4), preferring the latter products at the expense of the former with the increase of the electron-donating ability of the carbonion species. A SET mechanism is proposed for the conjugate addition.

Original languageEnglish
Pages (from-to)4821-4824
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number27
DOIs
Publication statusPublished - 1995 Jul 3

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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