Chemistry of (triphenylphosphoranylidene)sulfamoyl chloride. I. Reaction with amines and alcohols

Article abstract of DOI:10.1021/ic50148a005

Compounds of the type Ph₃PNSO₂OR and Ph₃PNSO₂NHR (R = Me, Et, n-Pr, n-Bu, and o-, m-, p-BrC₆H₄) have been prepared in good yield by the reaction of (triphenylphosphoranylidene)sulfamoyl chloride, Ph₃PNSO₂Cl, with alcohols in pyridine or with amines in chloroform; derivatives of secondary amines may also be prepared by the latter method. Heating the methyl ester in pyridine to moderately high temperatures produces a compound containing the Ph₃PNSO₂O^- ion which yields the free acid upon acidification. The infrared spectra of the title compound and the alkyl esters in the 1100-1300-cm^-1 region are presented and discussed.