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Synlett 2000; 2000(1): 49-52
DOI: 10.1055/s-2000-6475
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A Novel Synthesis of 1,2-Dialkylthio- and 2-Alkoxy-1-alkylthioethenes from β-Arylthioalkenylselenonium Salts and Its Application to the Synthesis of Medium-Membered Heterocycles Containing S and O Atoms

Shin-ichi Watanebe* , Eiji Mori, Hirotada Nagai, Tadashi Kataoka
  • *Gifu Pharmaceutical University, 6-1, Mitahora-higashi 5-chome, Gifu 502-8585, Japan; Fax + 81-58-237-5979; E-mail: kataoka@gifu-pu.ac.jp
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Publication Date:
31 December 2000 (online)

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The treatment of alkynylselenonium salts and thiophenol derivatives with a catalytic amount of triethylamine afforded β-arylthiovinylselenonium salts in good yields. The reactions of the vinylselenonium salts with nucleophiles produced (Z)-β-arylthio-α-functionalized ethenes in high yields. In addition, the vinylselenonium salts bearing a hydroxy group, 2d-f, 2h, underwent intramolecular cyclization upon treatment with sodium hydride to produce medium-membered heterocyclic compounds containing S and O atoms.

selenonium salt - Michael addition - heterocycles - ring closure - ligand coupling