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

Abstract

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
Volume89
Issue number9
DOIs
StatePublished - 1967
Externally publishedYes

Fingerprint

Dive into the research topics of 'Stereospecific Introduction of Azide Functions into Organic Molecules'. Together they form a unique fingerprint.

Cite this