Organosulfur Chemistry II

Volume 205 of the series Topics in Current Chemistry pp 131-195


Chemistry of Thiophene 1,1-Dioxides

  • Juzo NakayamaAffiliated withDepartment of Chemistry, Faculty of Science, Saitama University
  • , Yoshiaki SugiharaAffiliated withDepartment of Chemistry, Faculty of Science, Saitama University

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Thiophene oxides, where two pairs of lone pair electrons are consumed for bond formation with oxygen atoms, are no longer aromatic. Their chemistry has now grown into an important branch both in heteroatom and heterocyclic chemistry from synthetic, mechanistic, structural, and theoretical points of views. Thiophene 1,1-dioxides are most commonly prepared by oxidation of thiophenes. As unsaturated sulfones, they serve as dienophiles, 1,3-dipolarophiles, and Michael acceptors. They, as dienes, undergo a wide variety of synthetically useful Diels-Alder reactions and occasionally undergo even [4+6] cycloadditions. Many important reactions, which are not included in these categories, are also known. The present article describes the chemistry of thiophene 1,1-dioxides, with special emphasis being placed on their synthesis and synthetic applications. Many references on structural and theoretical studies are also given. The chemistry selenophene 1,1-dioxides is referred simply.


Thiophene selenophene oxidation cycloaddition Michael addition