Addition of Nitryl Iodide to Olefins

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

doi:10.1021/jo01261a030

Addition of Nitryl Iodide to Olefins

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

University of Colorado Boulder

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	2628-2632
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	34
Issue number	9
DOIs	https://doi.org/10.1021/jo01261a030
State	Published - Sep 1969
Externally published	Yes

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title = "Addition of Nitryl Iodide to Olefins",

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.",

author = "Alfred Hassner and Kropp, \{James E.\} and Kent, \{Gerald J.\}",

year = "1969",

month = sep,

doi = "10.1021/jo01261a030",

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AU - Kropp, James E.

AU - Kent, Gerald J.

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N2 - 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.

AB - 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.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Addition of Nitryl Iodide to Olefins

Abstract

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