Regiochemistry of Halogen Azide Addition to Allenes

Alfred Hassner, Joseph Keogh

Research output: Contribution to journalArticlepeer-review

29 Scopus citations


Iodine azide was found to undergo monoaddition to alkyl-substituted allenes 8–11, producing regioselectively allyl azides that can undergo [3,3]-rearrangement. Allene itself is an exception and adds IN3 at room temperature to form a bisadduct, shown to have a gem-diazide structure and to be derived from a vinyl azide monoadduct. BrN3 tends to behave as an ionic reagent analogous to IN3 at –65 °C, but at room temperature it adds to allenes in a free radical manner, leading to bisadducts which are unstable and can decompose explosively. The chemistry of the adducts was briefly explored.

Original languageEnglish
Pages (from-to)2767-2770
Number of pages4
JournalJournal of Organic Chemistry
Issue number14
StatePublished - 1986


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