Synlett · 2001 · 34 citations · 0 references
Natural SciencesChemistryGreen ChemistryOrganic ChemistryOrganometallic ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisAzone Derivatives
One-pot conversion of azides to N-monomethylamines is described. Two optional protocols have been developed, which share the first stage, the reaction of an azide with (CH 3 ) 3 P to generate the corresponding iminophosphorane. This Staudinger intermediate, thus generated, is either methylated with CH 3 I and hydrolyzed (method A), or treated with (HCHO) n and reduced with NaBH 4 (method B), thereby giving the corresponding N-monomethylamine in high yield.