Spirocyclic Meisenheimer complexes: XLIII. N-picryl derivatives of 1-acyl-2-(alkylsulfonyl)hydrazines: Formation of anionic spirocomplex with Delta(2)-1,3,4-oxadiazoline ring, and rearrangement

The reaction of N-[(benzylthio)acetyl]-N '-(alkylsulfonyl)hydrazines with p icrylfluoride in the presence of triethylamine gives rise to regioselective formation of N-(alkylsulfonyl)-N-picryl-N '-[(benzylthio)acetyl]hydrazines that further transform into anionic complexes with Delta (2)-1,3,4-oxadiaz oline cycle spiro joined with 2,4,6-trinitrocyclohexadienate system. Unlike that in the reaction of N-furoyl-N '-(ethylsulfonyl)hydrazine with picryl fluoride under similar conditions the primary product undergoes rearrangeme nt to yield N-furoyl-N-(ethylsuifonyl)-N ' -picrylhydrazine.