A CONVENIENT CONVERSION OF PRIMARY AMINES INTO THE CORRESPONDING HALIDES-RADICAL PROMOTED HALODEAMINATION VIA N-SUBSTITUTED-N-TOSYLHYDRAZINES

Authors
COLLAZO LR GUZIEC FS HU WX PANKAYATSELVAN R
Citation
Lr. Collazo et al., A CONVENIENT CONVERSION OF PRIMARY AMINES INTO THE CORRESPONDING HALIDES-RADICAL PROMOTED HALODEAMINATION VIA N-SUBSTITUTED-N-TOSYLHYDRAZINES, Tetrahedron letters, 35(43), 1994, pp. 7911-7914
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
43
Year of publication
1994
Pages
7911 - 7914
Database
ISI
SICI code
0040-4039(1994)35:43<7911:ACCOPA>2.0.ZU;2-U
Abstract
Treatment of 1-substituted-1-tosylhydrazines with 2 equivalents of NCS or NBS in dry THF in presence of light affords the corresponding alky l halides in good yields. This reaction presumably involves the initia l formation of a stabilized hydrazyl radical which is halogenated in a radical chain process. Elimination of p-toluenesulfinic acid and extr usion of nitrogen leads to the corresponding alkyl halide. This route provides an improved method for halodeamination under neutral reaction conditions.