title: Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters.
abstract: [reaction: see text] 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.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60201-3113, USA.
authors.forename: J A
authors.initials: JA
authors.lastname: Gómez-Vidal
authors.forename: M T
authors.initials: MT
authors.lastname: Forrester
authors.forename: R B
authors.initials: RB
authors.lastname: Silverman
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D007202:Indicators and Reagents; D009579:Nitrobenzoates / Q000737:chemistry*; D019810:Sodium Azide / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D004952:Esters; D007202:Indicators and Reagents; D009579:Nitrobenzoates; D019810:Sodium Azide; C008629:4-nitrobenzoic acid