A Convenient Conversion of Primary Amines into the Corresponding Halides Radical Promoted Halodeamination via N-Substituted-N-Tosylhydrazines
Treatment of 1-substituted-1-tosylhydrazines with 2 equivalents of NCS or NBS in dry THF in presence of light affords the corresponding alkyl halides in good yields.This reaction presumably involves the initial formation of a stabilized hydrazyl radical which is halogenated in a radical chain process.Elimination of p-toluenesulfinic acid and extrusion of nitrogen leads to the corresponding alkyl halide.This route provides an improved method for halodeamination under neutral reaction conditions.
Collazo, Luis R.,Guziec, Frank S.,Hu, Wei-Xiao Jr.,Pankayatselvan, Ratnadevi
p. 7911 - 7914
(2007/10/02)
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