NUCLEOPHILIC SUBSTITUTION AT NITROGEN-CENTERED RADICALS: REACTIONS OF DIPHENYLPHOSPHIDE IONS WITH N,N-DIBUTYL-p-TOLUENESULFONAMIDE BY THE S_(RN)1 MECHANISM

摘要

The 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 S_(RN)1 mechanism.