Facile Method for the Synthesis of Vicinal Azidoiodides by the Reaction of the NaN₃–I₂ System with Unsaturated Compounds

Abstract

A facile and efficient method was developed for the synthesis of vicinal azidoiodides in 62–77% yields by the reaction of sodium azide and iodine with unsaturated compounds in methanol, aqueous methanol, or the water–methanol–tetrahydrofuran solvent system. The reaction in Et₂O or CHCl₃ produced only vicinal diiodides.

Keywords:

• Alkenes
• azides
• azidoiodination
• iodine
• sodium azide

Notes

^a Reaction conditions: sodium azide (0.618 g, 9.5 mmol, 2 mol/1 mol 1a) was added to a solution of 1a (0.4 g, 4.75 mmol) in the solvent (10 ml), and then I₂ (1.81 g, 7.13 mmol, 1.5 mol/1 mol 1a) was added with stirring at 20–25°C. The reaction mixture was stirred for 1.5 h.

^b The v/v ratio.

^a The yield based on the isolated product.

^b Experiments on the synthesis of 2b, c, e, and f were scaled with an increase in the amounts of the reagents by a factor of 10.