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Interaction of certainα-dicarbonyl compounds with ethanedithiol and steric structure of the products formed

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Conclusions

  1. 1.

    1-Phenylpropane-1,2-dione gives a bis-1,3-dithiolane derivative in the reaction with 1,2-ethanedithiol, analogously to glyoxal and phenylglyoxaL Diacetyl and benzil give the corresponding monomercaptals.

  2. 2.

    1-Phenylpropane-1,2-dione is reduced in the reaction with 1,2-ethanedithiol, forming 2-ethyl-2-phenyl-1, 3-dithiolane,

  3. 3.

    Bis-1,3-dithiolane derivatives of 1-phenylpropane-1, 2-dione, glyoxal, and phenylglyoxal exist in the gauche-form; 2-keto-l,3-dithiolanes from diacetyl and benzil have shielded structures with predominance of the S-conformer.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2422–2426, November, 1973.

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Arbuzov, B.A., Klimovitskii, E.N., Yuldasheva, L.K. et al. Interaction of certainα-dicarbonyl compounds with ethanedithiol and steric structure of the products formed. Russ Chem Bull 22, 2368–2371 (1973). https://doi.org/10.1007/BF00926373

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Keywords

  • Dione
  • Diacetyl
  • Glyoxal
  • Dithiolane
  • Benzil