An unexpected [1,5]-H shift in the synthesis of nitroanilines

Ian W. Davies, Jean François Marcoux, Jeremy D.O. Taylor, Peter G. Dormer, Robert J. Deeth, Félix Antoine Marcotte, David L. Hughes, Paul J. Reider

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Equation Presented Addition of methyl acetoacetate to 2-nitrovinamidinium hexafluorophosphate salts leads to the formation of anilines or phenols in good to excellent yields depending on the alkylamine substituents. Small substituents, e.g., pyrrolidine, lead to the formation of anilines while large substituents, e.g., N,N-diisopropyl, exclusively give phenols. Labeling studies implicate a [1,5]-H shift proceeding with excellent isotopic fidelity.

Original languageEnglish (US)
Pages (from-to)439-441
Number of pages3
JournalOrganic Letters
Volume4
Issue number3
DOIs
StatePublished - Feb 7 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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