Iodosobenzene, with sodium azide

The reaction of alkenes with iodosobenzene in acetic acid in the presence of sodium azide offers a simple and high yield route to 1,2-diazides (Table 3)76. a-Azido ketones are side products or the exclusive product from the reaction with conjugated alkenes. Allylic azides or oxonitriles, resulting from oxidative cleavage of the C-C double bond, are alternatively obtained from trisubstituted steroid alkenes77. 

Two azido groups can be added to double bonds by treatment with sodium azide and iodosobenzene in acetic acid." ... 

To a solution of iodosobenzene (2.2 g, 10 mmol) and 5 (1.79 g, 5 mmol) in acetic acid (30 ml) sodium azide (2.3 g, 35 mmol) was added. The mixture was maintained at room temperature for 10 min then kept at 50 °C for 3 hours, then poured into water (200 ml) and extracted with chloroform (4 x 50 ml). The combined extracts were washed with water (2 x 100 ml), dried mgS04), and evaporated. The residue was chromatographed on silica gel (60 mesh) elution with benzene-pet. -ether (1 1) 6 (1.27 g, 64%). 

Table 3. 1,2-Diazides by Reaction with Sodium Azide and Iodosobenzene in Acetic Acid76...

The direct azido phenylselenenylation of alkenes can be accomplished by four different methods A126 reaction with phenylselenenyl chloride and sodium azide in dimethyl sulfoxide or dimethylformamide B127 reaction with diphenyldiselenide, sodium azide and iodosobenzene diacetate in dichloromethane C128 reaction with iV-phenylselenophthalimide (TV-PSP) and azidotrimethylsilane in dichloromethane D128 as in C but in the presence of 0.1 equivalent of tetrabutylammonium fluoride. 

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