Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters

José A. Gómez-Vidal, Michael T. Forrester, Richard B. Silverman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Scopus citations


matrix presented A mild and selective cleavage of p-nitrobenzoic esters by sodium azide in methanol is reported. This new methodology is mild enough for use with acid-or base-sensitive compounds. No elimination byproducts are formed. Fmoc-and trifluoroacetyl-amino protecting groups, benzyl esters, and ethyl esters remain unaffected. Less reactive compounds are discussed in terms of steric factors, and yields are increased by altering the azide solvation.

Original languageEnglish (US)
Pages (from-to)2477-2479
Number of pages3
JournalOrganic Letters
Issue number16
StatePublished - Aug 9 2001

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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