Addition of Nitryl Iodide to Olefins

Alfred Hassner, James E. Kropp, Gerald J. Kent

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55 Scopus citations


The reaction of silver nitrite with iodine in the presence of olefins was studied and was found to lead to nitroiodo adducts. The reaction has the characteristics of a nitryl iodide addition and appears to proceed by a free-radical attack of an NO2 species on the double bond. Stereochemical and regiochemical considerations are discussed. The method provides a selective synthesis of β-iodonitro-, vinylnitro-, and nitroalkanes under mild reaction conditions.

Original languageEnglish
Pages (from-to)2628-2632
Number of pages5
JournalJournal of Organic Chemistry
Issue number9
StatePublished - Sep 1969
Externally publishedYes


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