Studies on the Sulfurcontaining Chelating Agents. XIII. Syntheses of Esters of β-Mercaptothiocinnamic Acid and their Structures.

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Abstract

Esters of β-mercaptothiocinnamic acid were prepared as strong chelating agents. Phenylpropioloyl chloride was converted into alkyl or aryl phenylthiopropiolate and thiourea was reacted in the presence of p-toluenesulfonic acid to obtain corresponding isothiuronium salts. Esters of β-mercaptothiocinnamic acid were obtained by the hydrolyses of the isothiuronium salts. Thioxo-thioenol tautomerism in the esters of β-mercaptothiocinnamic acid was investigated by infrared and nuclear magnetic resonance spectroscopy. It was found that cis-thioenol form is predominant and hence the mercapto group and the carbonyl group are markedly hydrogen-bonded.

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