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Reaction of α-cyanoacrylates with functionally substituted thiols, ethanedithiol, and hydrogen sulfide

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

Functionally substituted thiols, i.e., thioglycolic acid and cysteamine and cysteine hydrochlorides, facilely undergo addition at the double bond of α-cyanoacrylates, forming the corresponding adducts in quantitative yields: R′SCH2CH(CN)COOR [R′=CH2COOH; CH2CH2NH2·HCl; CH2CH(COOH)NH2·HCl]. Under similar conditions, the reaction with ethanedithiol gives the diadduct [CH2SCH2CH(CN)COOR]2; the monoadduct HSCH2CH2SCH2CH(CN)COOR is formed in a significantly lower yield. Hydrogen sulfide does not undergo addition to α-cyanoacrylate in the absence of a catalyst; S[CH2CH(CN)COOR]2 is formed quantitatively in the presence of Et3N. In the presence of triethylamine, this sulfide undergoes intramolecular cyclization (the Ziegler-Thorpe reaction) with formation of 4-amino-5-cyano-3,5-bis(ethoxycarbonyl)thiacyclohex-3-ene.

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Literature cited

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    I. I. Kandror, I. O. Bragina, M. A. Galkina, T. I. Guseva, B. D. Lavrukhin & Yu. G. Gololobov

Authors
  1. I. I. Kandror
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  2. I. O. Bragina
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  3. M. A. Galkina
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  4. T. I. Guseva
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  5. B. D. Lavrukhin
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  6. Yu. G. Gololobov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2816–2820, December, 1991.

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Kandror, I.I., Bragina, I.O., Galkina, M.A. et al. Reaction of α-cyanoacrylates with functionally substituted thiols, ethanedithiol, and hydrogen sulfide. Russ Chem Bull 40, 2456–2459 (1991). https://doi.org/10.1007/BF00959721

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  • DOI: https://doi.org/10.1007/BF00959721

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