Mechanism of oxidation of α,β-unsaturated thiones by singlet oxygen

V. Pushkara Rao, V. Ramamurthy

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Photo-oxidation of α,β-unsaturated thiones yields the corresponding ketones as the only product. Studies carried out on three systems, namely thioketones, α,β-unsaturated thiones and thioketenes, have revealed that there exists a similarity in their mechanism of oxidation. It has been suggested that the thiocarbonyl chromophore is the site of attack by singlet oxygen in α,β-unsaturated thiones and that the adjacent C-C double bond is inert under these conditions. Absence of sulphine during the oxidation of α,β-unsaturated thiones is attributed to the electronic factors operating on the zwitterionic/diradical intermediate. While α,β-unsaturated ketones are poorly reactive, α,β-unsaturated thiones are highly reactive toward singlet oxygen.

Original languageEnglish (US)
Pages (from-to)2169-2176
Number of pages8
JournalTetrahedron
Volume41
Issue number11
DOIs
StatePublished - 1985
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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