Studies on Thiohydroxamic Acids and Their Metal Chelates. I. Syntheses of Thiohydroxamic Acids and O-Methyl-thiohydroxamic Acids

Abstract

Nineteen kinds of sodium thiohydroxamate (I) were synthesized from hydroxylamine and esters of thionic acids or dithioacids in the presence of sodium methylate with about 40% yields for the aliphatic compounds and above 70% yields for the aromatic ones with some exceptions. A number of sodium O-methylthiohydroxamate (II) were also obtained by the analogous method using O-methylhydroxylamine. On long standing. I were apt to rearrange to the 1, 3-disubstituted thiourea while II were very stable. Some crystalline thiohydroxamic acid and O-methylthiohydroxamic acids were prepared from I and II.