Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters.
[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.
Gomez-Vidal,Forrester,Silverman
p. 2477 - 2479
(2007/10/03)
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