Addition of Nitryl Iodide to Olefins

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

Research output: Contribution to journalArticlepeer-review

55 Scopus citations

Abstract

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
Volume34
Issue number9
DOIs
StatePublished - Sep 1969
Externally publishedYes

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