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Opening of the Furan Ring of 3-Nitrobenzofurans by the Action of Carbonyl-Stabilized Sulfonium ylides

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Chemistry of Heterocyclic Compounds Aims and scope

Upon treatment of 3-nitrobenzofurans with dimethylphenacylsulfonium salts in the presence of a base, the opening of the furan ring to form (E)-1-aryl-2-(dimethylsulfonio)-4-nitro-1-oxobut-3-en-2-ides takes place. The mechanism of nucleophilic dearomatization of 3-nitrobenzofurans involves consecutive carbo- and retro-oxa-Michael reactions. The reaction illustrates the high propensity of 3-nitrobenzofurans for ring opening.

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya St, Samara, 443100, Russia

    Irina А. Semenova, Vitaly А. Osyanin & Dmitry V. Osipov

  2. North Caucasus Federal University, 1a Pushkina St, Stavropol, 355009, Russia

    Oleg P. Demidov

Authors
  1. Irina А. Semenova
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  2. Vitaly А. Osyanin
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  3. Oleg P. Demidov
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  4. Dmitry V. Osipov
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Corresponding authors

Correspondence to Vitaly А. Osyanin or Dmitry V. Osipov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 251–254

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Semenova, I.А., Osyanin, V.А., Demidov, O.P. et al. Opening of the Furan Ring of 3-Nitrobenzofurans by the Action of Carbonyl-Stabilized Sulfonium ylides. Chem Heterocycl Comp 58, 251–254 (2022). https://doi.org/10.1007/s10593-022-03079-6

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  • DOI: https://doi.org/10.1007/s10593-022-03079-6

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