Nitroxide chemistry. Part 15. Reactions between bistrifluoromethyl nitroxide and benzyl alcohol, azide, chloride, and cyanide

Abstract

Bistrifluoromethyl nitroxide readily attacks benzyl cyanide and benzyl chloride at room temperature to give the α-bistrifluoromethylamino-oxy-derivatives PhCHRCN and PhCHRCl [R =–ON(CF3)2] respectively; treatment of the former product with the nitroxide yields benzoyl cyanide and the di-substituted derivative PhCR2CN. Abstraction of a benzylic hydrogen atom by the nitroxide from benzyl alcohol and benzyl azide leads, respectively, to the formation of benzaldehyde (and hence PhCOR) and benzonitrile.