Reactions of N,N-diisopropyl-2-aminoethyl p-fluorobenzene thiosulfonate with oxidising agents

The behaviour of N,N-diisopropyl-2-aminoethyl p-fluorobenzene thiosulfonate 3, which may be considered as a weakly toxic chemical analogue of VX agent, was investigated against oxidising agents. as VX 1, this compound exhibits the same tendency to give S-S bond cleavage. Its degradation by Curox (R) shows the formation of the N-oxide 6 which subsequently ives the sulfonate 7 by hydrolysis. The action of hydrogen peroxide, with or without boric acid, leads to the sulfinate 4 by S-S bond cleavage. Its oxidation gives sulfonate 7. Finally, reactions of MMPP and m-CPBA afford sulfonate 7 but no intermediates are highlighted with these reagents. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevier SAS.