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.
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.