Stereospecific Introduction of Azide Functions into Organic Molecules

Frank W. Fowler, Alfred Hassner, Louis A. Levy

Research output: Contribution to journalArticlepeer-review

327 Scopus citations


Iodine azide prepared in situ by the reaction of sodium azide and iodine monochloride in acetonitrile has been shown to add in good yield and in a highly stereospecific manner to a variety of unsaturated systems. Thus, cyclohexene and 2-cholestene produce the trans and the trans-diaxial adduct, respectively; straight-chain cis and trans olefins give respectively the threo and erythro adducts; terminal olefins form adducts where the azido function is at the 2 position; and conjugated olefins such as 1,2-dihydronaphthalene lead to products with the azido function occupying the benzylic position. Tolane and 1,3-cyclooctadiene yield one-to-one adducts; conjugated ketones and esters give adducts where the azido function occupies the β position; and isonitriles give iodotetrazoles. Possible mechanisms for these reactions are discussed.

Original languageEnglish
Pages (from-to)2077-2082
Number of pages6
JournalJournal of the American Chemical Society
Issue number9
StatePublished - 1967
Externally publishedYes


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