Iron-mediated radical halo-nitration of alkenes.
Radical halo-nitration of alkenes using iron(III) nitrate nonahydrate and halogen salt has been developed. The present reaction proceeds 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 halogen salt. Application of this method to synthesis of nitroalkenes is also described. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the application to broad alkenes.
School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. tsuyoshi@p.kanazawa-u.ac.jp
Tsuyoshi
T
Taniguchi
Tatsuya
T
Fujii
Hiroyuki
H
Ishibashi
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D005290:Ferric Compounds / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D009566:Nitrates / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D009585:Nitrogen Dioxide / Q000737:chemistry*
D000475:Alkenes; D005290:Ferric Compounds; D006846:Hydrocarbons, Halogenated; D009566:Nitrates; D009574:Nitro Compounds; D009585:Nitrogen Dioxide