Photochemical oxidation of thioketones: Steric and electronic aspects

N. Ramnath, V. Ramesh, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

54 Citations (Scopus)

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
Pages (from-to)214-222
Number of pages9
JournalJournal of Organic Chemistry
Volume48
Issue number2
StatePublished - Dec 1 1983
Externally publishedYes

Fingerprint

Ketones
Singlet Oxygen
Oxidation
Chromophores
Oxygen

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Photochemical oxidation of thioketones : Steric and electronic aspects. / Ramnath, N.; Ramesh, V.; Ramamurthy, Vaidhyanathan.

In: Journal of Organic Chemistry, Vol. 48, No. 2, 01.12.1983, p. 214-222.

Research output: Contribution to journalArticle

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