New reaction of dithiophosphoric acids with O-thioacylhydroxylamines. Nucleophilic substitution or single electron transfer process?

摘要

Disubstituted or sterically hindered hydroxylamines react with bulky S-thioacyl dithiophosphates yieldingnO-thioacylhydroxylamines. The reaction of O-thioacylhydroxylamines with dithiophosphoric acids yields acylnthiophosphoryl disulfides and ammonium dithiophosphates. The influence of radical traps on the reactionnyield strongly suggests that radicals are involved in the mechanism of the process. The low redox potential ofndithiophosphates, the observed photochemical stability of O-thioacylhydroxylamines and the influence of lightnon acyl thiophosphoryl disulfides yield imply involvement of a single electron transfer process in the investigatednreaction.