&β-(N,N-Dialkylamino)ethyl Arylthiosulfonates: New Simulants for O-Ethyl S- Methylphosphonothioate

Article abstract of DOI:10.1021/jo00035a013

β-(N,N-Dialkylamino)ethyl arylthiosulfonates 2, new simulants for the hydrolysis and oxidation chemistry of VX (1), are prepared in good yield by reaction of a potassium arylthiosulfonate with a 2-chloroethylamine.Alkaline hydrolysis of 2 results in cleavage of the S-S-bond to give sulfinic acids and disulfides.Like VX, oxidation of 2 by N-sulfonyloxaziridine 12 occurs exclusively on nitrogen to give the corresponding amine oxide which subsequently undergoes a Cope elimination reaction affording the vinyl sulfide 14.