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Interference of two adjacent methoxy groups as promoters of arene metallation

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
41
Issue
23
Identifiers
DOI: 10.1016/s0040-4039(00)00683-3
Keywords
  • Metallation
  • Ortho-Lithiation
  • Heteroatom Facilitated Litiation
  • Hydrogen–Metal Exchange

Abstract

Abstract Two adjacent methoxy groups on a benzene ring reinforce each other as promoters of ortho-lithiation; the lower ease of metallation of veratrole with repect to anisole, observed in one special case, can be explained by the deactivation of the substrate upon formation of a chelate species with the lithium atom of the metallating agent.

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