A convenient conversion of primary amines into the corresponding halides—Radical promoted halodeamination via N-substituted-N-Tosylhydrazines
LR Collazo, FS Guziec, WX Hu, R Pankayatselvan
Index: Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi Tetrahedron Letters, 1994 , vol. 35, # 43 p. 7911 - 7914
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Citation Number: 7
Abstract
Abstract 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 ...
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