{ALF} Azides can be converted selectively to amines, in the presence of ester, epoxide or nitro groups, by reduction to iminophosphoranes (Staudinger reaction), followed by hydrolysis. For reviews, see: Tetrahedron, 37, 437 (1981); 48, 1353 (1992):

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{ALF} Finds widespread use as a complexing agent with transition metals, either in the preparation of stable complexes, or as an additive in metal-promoted reactions. See also Tri(o-tolyl)­phosphine, A12093 and Tri(2-furyl)­phosphine, L13329.

{ALF} For use in peptide and other coupling reactions, see 2,2'-Dipyridyl­ disulfide, A11118.

{ALF} For use in the Mitsunobu reaction for conversion of alcohols to alkylating agents, see N-Guanyl­urea sulfate, A19106, and Diisopropyl­ azodicarboxyl­ate, L10386. See also 1,2-Bis(diphenyl­phosphino)­ethane, A11419.

{ALF} In suitable circumstances, the iminophosphorane may undergo intramolecular aza-Wittig reaction: Tetrahedron, 45, 6375 (1989):

{ALD} Merck: 14,9743

{ALD} Merck: 14,9743 Beilstein:16,759

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