Conclusions
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1.
The reaction ofβ-chlorosulfenylcarboxylic acids with CH3COSH gave the correspondingβ-(acetyldithio) carboxylic acids, reaction with H2S gave di-(β-carboxy) andβ-carbomethoxyethyl)trisulfides, while reaction with C6H5MgBr gave the methyl esters ofβ-Cphenylthio)- andα-chloro-β-(phenylthio)propionic acids.
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2.
The presence of chlorine atomsα-, and especiallyβ-) in theβ-cblorosulfenylcarboxylic acids lowers the reactivity of the SCI group toward weak nucleophiles.
Literature cited
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W. H. Mueller, J. Org. Chem.,34, 2955 (1969).
M. G. Lin'kova, L. P. Parshina, Z. K. Stumbrevichute, O. V. Kil'disheva, and I. L. Knunyants, Dokl. Akad. Nauk SSSR,196, 1089 (1971).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2379–2382, October, 1973.
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Vasil'eva, T.P., Lin'kova, M.G., Kil'disheva, O.V. et al. Derivatives ofβ- chlorosulfenylcarboxylic acids and their reactions with nucleophilic reagents. Russ Chem Bull 22, 2327–2329 (1973). https://doi.org/10.1007/BF01199651
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DOI: https://doi.org/10.1007/BF01199651