Photochemical Oxidation of Thioketones: Steric and Electronic Aspects

N. Ramnath, V. Ramesh, V. Ramamurthy

Research output: Contribution to journalArticle

55 Scopus citations

Abstract

Oxidation of diaryl, aryl alkyl, and dialkyl thioketones by singlet oxygen generated via self-sensitization and other independent methods yielded the corresponding ketone and sulfine in varying amounts. A zwitterionic/diradical intermediate arising out of the primary interaction of singlet oxygen with the thiocarbonyl chromophore is believed to be the common intermediate for the ketone and sulfine. While closure of the zwitterion/diradical to give 1,2,3-dioxathietane would lead to the ketone, competing oxygen elimination is believed to lead to the sulfine. This partitioning is governed by steric and electronic factors operating on the zwitterionic/diradical intermediate.

Original languageEnglish (US)
Pages (from-to)214-222
Number of pages9
JournalJournal of Organic Chemistry
Volume48
Issue number2
DOIs
StatePublished - Jan 1983
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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