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

V. Pushkara Rao, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

11 Citations (Scopus)

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
Pages (from-to)2169-2176
Number of pages8
JournalTetrahedron
Volume41
Issue number11
DOIs
StatePublished - Jan 1 1985
Externally publishedYes

Fingerprint

Thiones
Singlet Oxygen
Oxidation
Ketones
Photooxidation
Chromophores

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Mechanism of oxidation of α,β-unsaturated thiones by singlet oxygen. / Rao, V. Pushkara; Ramamurthy, Vaidhyanathan.

In: Tetrahedron, Vol. 41, No. 11, 01.01.1985, p. 2169-2176.

Research output: Contribution to journalArticle

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