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Nucleophilic sulfanylation of 1,5-disubstituted pent-2-en-4-yn-1-ones

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Abstract

Regioselectivity of nucleophilic addition of benzenethiols and phenylmethanethiol to 1,5-diarylpent-2-en-4-yn-1-ones in ethanol in the presence of triethylamine at 0–30°C is determined by the nucleophile nature. Phenylmethanethiol adds to the double bond, whereas benzenethiols add to the triple bond. The addition products, 1,5-diaryl-3-benzylsulfanylpent-4-yn-1-ones and 1,5-diaryl-5-(4-arylsulfanyl)penta-2,4-dien-1-ones, respectively, were isolated in 43–89% yield. Substituents in the aryl rings of the substrates did not affect the reaction direction.

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Authors and Affiliations

  1. Togliatti State University, ul. Belorusskaya 14, Togliatti, 445667, Russia

    A. A. Golovanov, D. M. Gusev, V. V. Bekin & V. S. Pisareva

  2. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    A. V. Vologzhanina

Authors
  1. A. A. Golovanov
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  2. D. M. Gusev
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  3. A. V. Vologzhanina
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  4. V. V. Bekin
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  5. V. S. Pisareva
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Correspondence to A. A. Golovanov.

Additional information

Original Russian Text © A.A. Golovanov, D.M. Gusev, A.V. Vologzhanina, V.V. Bekin, V.S. Pisareva, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 21–28.

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Golovanov, A.A., Gusev, D.M., Vologzhanina, A.V. et al. Nucleophilic sulfanylation of 1,5-disubstituted pent-2-en-4-yn-1-ones. Russ J Org Chem 50, 13–20 (2014). https://doi.org/10.1134/S1070428014010035

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  • DOI: https://doi.org/10.1134/S1070428014010035

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