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

T. Hattori, N. Koike, T. Satoh, S. Miyano

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

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 carbanion 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
Publication statusPublished - 1995 Jan 1

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Reaction of benzoic esters with organolithium and -magnesium reagents. Dichotomy between nucleophilic aromatic substitution and conjugate addition'. Together they form a unique fingerprint.

Cite this