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Please login to access the full content or check if you have access via Method 4: Azido- and Aminoiodination of Alkenes

DOI: 10.1055/sos-SD-035-00601

Troll, T.Science of Synthesis, (200735731.

Organic azides are of interest due to their photochemistry, cycloaddition reactions, and as precursors to amino groups.[‌41‌] Iodine azide is described as highly explosive, but can be prepared and handled safely in solution.[‌42‌‌44‌] Addition of alkenes to solutions of iodine azide in acetonitrile at 10 to 25°C gives adducts in excellent yields. The addition is stereospecific, with (E)- or (Z)-but-2-ene furnishing exclusively erythro- or threo-2-azido-3-iodobutane, respectively (Scheme 21).[‌43‌,‌44‌]

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