Tetrahedron

The functionalization of saturated hydrocarbons. Part 25. Ionic substitution reactions in GoAgg IV chemistry: the formation of carbon-halogen bonds

DHR Barton, SD Bévière, W Chavasiri

Index: Barton, Derek H. R.; Beviere, Stephane D.; Chavasiri, Warinthorn Tetrahedron, 1994 , vol. 50, # 1 p. 31 - 46

Full Text: HTML

Citation Number: 20

Abstract

GoAggIV chemistry (Fe (III) species, tert-butyl hydroperoxide in a mixture of pyridine and acetic acid) in the presence of LiCl can transform saturated hydrocarbons efficiently into the corresponding alkyl chlorides. The transformation into monosubstituted alkyl derivatives by “ionic trapping” reagents arising from the interception of the first intermediate of the system supports the presence of a high valent VFe-C species. Mechanistic studies suggest a ...