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Iron-Mediated Radical Halo-Nitration of Alkenes

Tsuyoshi Taniguchi*, Tatsuya Fujii and Hiroyuki Ishibashi

*School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan, Email: tsuyoship.kanazawa-u.ac.jp

T. Taniguchi, T. Fuji, H. Ishibashi, J. Org. Chem., 2010, 75, 8126-8132.

DOI: 10.1021/jo101769d (free Supporting Information)


Abstract

Radical halo-nitration of alkenes proceeds easily by radical addition of nitrogen dioxide generated by thermal decomposition of iron(III) nitrate nonahydrate and subsequent trapping of the resultant radical by a halogen atom in the presence of a halogen salt. Application of this method to synthesis of nitroalkenes is also described.

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Key Words

Nitration, Chlorination, Nitro Alkenes


ID: J42-Y2010-3390