New Alkane Functionalization Reactions Based on Gif-Type Chemistry in the Presence of Alkali Metal Salts.

Article abstract of DOI:10.1016/S0040-4039(00)91950-6

Cycloalkanes are transformed into monosubstituted cycloalkyl derivatives (chloride, azide, cyanide, thiocyanate, dicycloalkyl disulfide, or nitroalkane) in mostly good efficiencies by treatment with tert-butyl hydroperoxide in pyridine/acetic acid containing Fe(NO3)3*9H2O, in the presence of alkali metal salts (LiCl, NaN3, CN, NaSCN, Na2S, or NaNO2, respectively).In comparison, ionic trapping with Cu(OAc)2 gave efficient trapping with chloride ion, very inefficient capture of thiocyanate, and a significant difference in reactivity towards azide ion.