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Synthesis 1971; 1971(1): 1-15
DOI: 10.1055/s-1971-21662
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Nitrogen Radicals as Synthesis Intermediates. N-Halamide Rearrangements and Additions to Unsaturated Hydrocarbons

R. S. NEALE*
  • *Union Carbide Chemicals and Plastics, Tarrytown Technical Center, Tarrytown, New York 10591, U.S.A.
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Publication Date:
12 September 2002 (online)

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N-Halamides, R-N(Hal)-X can be rearranged to halo-alkyl isomers in a manner analogous to the free-radical Hofmann-Löffler reaction of protonated N-chloramines. Addition of N-chloramides to unsaturated hydrocarbons also occurs to afford a variety of N-substituted ß-chloroalkyl compounds of the type, or related structures. Both types of reaction are reviewed for halamides with X=-CO-R, -COOR, -SO2-R, and -CN and compared with the corresponding reactions of protonated N-chloramines.