Abstract
Sulfonamides[1], [2]and[3]reacted with dialkylthio6arbamoyl chlorides[4]to give Nsulf ony1-1, N -dialkylthiocarbamoylisothio reas[5] and N, 1 -di-sulfonyl-N, X, -dialky1-guanidines[6].The Iatter compounds were found to be desulfurizing condensation products from[5]and excess sulfonamides. The favorable conditions for the syntheses of these compounds were determined. Fou methyl p otons of[5]showed non-equivalent.chemical shift due tothe restricted rotation of these methyl groups around the two C-N bonds. Acid-cataly2ed hydrolysesof[5 a 1]gave sulfonylthioureas[7], while the isothioureas of[5 n q]were not hydrolyzed under the same conditions. Base-catalyzed hydrolyses of [5] yielded sulfonylureas [8].
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