Nucleophilic substitution at nitrogen‐centered radicals: Reactions of diphenylphosphide ions with N,N‐dibutyl‐p‐toluenesulfonamide by the SRN1 mechanism

Abstract

AbstractThe photostimulated reaction of N,N‐dibutyl‐p‐toluenesulfonamide with diphenylphosphide ions in liquid ammonia leads to the corresponding phosphinic amides after oxidation Inhibition experiments with p‐dinitrobenzene and 2,2,6,6‐tetramethyl‐1‐piperidinyloxy free radical (TEMPO) and the fact that the reaction is retarded in the dark suggest that it proceeds by the SRN1 mechanism.