Studies on Thiohydroxamic Acids and Their Metal Chelates. III. Syntheses of Some Thiohydroxamic Acid Derivatives and Their Structures

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Thiohydroxamic acids react as thiol-form in aqueous solution, and gave S-alkyl and S, O-dialkyl derivatives, dibenzoyl derivatives, and the disulfides (I). Monobenzoyl derivatives were not obtained because of their instability. The structures of these derivatives were confirmed by the investigations of the infrared spectra. It was found that the S-S linkage of I are apt to cleave by alkali so that diacyl derivatives of I are easily rearragned to the corresponding isothiocyanate and 1, 3-dialkyl-2-thiourea. The mechanism of the rearrangement seemed to be analogous to that of the Lossen rearrangement.

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