2(5H)-Furanone Azides in the Synthesis of Iminophosphoranes and Amines

The synthesis and characterization of previously unknown azides, iminophosphoranes and amines from commercially available mucochloric and mucobromic acids is reported. The reaction of 5-alkoxy-3,4-dihalo-2(5H)-furanones with sodium azide resulted in the regioselective formation of furanone 4-azidoderivatives. A series of novel iminophosphoranes was obtained from the reaction of corresponding azides with triphenylphosphine. Reduction of iminophosphoranes with stannous chloride dihydrate led to the heterocycles, possessing an amino group at the C4 carbon atom of the unsaturated γ-lactone ring.