Tetrahedron Letters p. 7911 - 7914 (1994)
Update date:2022-09-26
Topics:
Collazo, Luis R.
Guziec, Frank S.
Hu, Wei-Xiao Jr.
Pankayatselvan, Ratnadevi
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.
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