REACTION OF NH-AZOLES WITH O-FLUOROSULFONYL-N,N-DIFLUOROHYDROXYLAMINE- SYNTHESIS OF N-FLUOROSULFONYLAZOLES

O-Fluorosulfonyl-N,N-difluorohydroxylamine (FH) reacts with anions of NH-azoles (imidazoles, pyrazoles, and 1,2,3-triazoles) to give the cor responding N-fluorosulfonylazoles, which were used to obtain N,N'-sulf onylbisazoles. The N-fluorosulfonylation proceeds at the nitrogen atom furthest from the most electron-withdrawing substituent in the azole ring. Nonaromatic NH-acid anions (imides and primary N-nitroamines) ar e sometimes capable of giving N-fluorosulfonyl derivatives although in yields less than 5 %. These products are much less stable than N-fluo rosulfonylazoles. The N-fluorosulfonylation presumably proceeds as nuc leophilic substitution at the sulfur atom of FH.