Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on the Sulfurcontaining Chelating Agents. XIII. Syntheses of Esters of β-Mercaptothiocinnamic Acid and their Structures.
横山 陽田中 久
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ジャーナル フリー

1964 年 12 巻 6 号 p. 683-689

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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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© The Pharmaceutical Society of Japan
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