Michel Desgranges

Comparative evaluation of oxidising and nucleophilic properties of some α-nucleophiles

Six α-nucleophiles were evaluated at pH = 8 in an aqueous methanolic solution for their oxidising power towards tetrahydrothiophene, and the nucleophilic properties towards paraoxon. MMPP and m-CPBA are the most versatile reagents and can act as nucleophiles as well as oxidising agents.

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

Abstract 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® shows the formation of the N- oxide 6 which subsequently gives 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.