Oxidations of thioketones by singlet and triplet oxygen

V. Jayathirtha Rao, K. Muthuramu, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Oxidation of di-tert-butyl thioketone (1) and 2,2,4,4-tetramethylcyclobutyl thioketone (2) by singlet oxygen yields the corresponding sulfine and ketone; in the case of 1 the sulfine is the major product, whereas in 2 it is the ketone. 1,2,3-Dioxathietane has been suggested as the precursor for the ketones, and the zwitterionic/diradical peroxide is believed to be a common primary intermediate for both sulfine and ketone. Steric influence is felt both during primary interaction between singlet oxygen and thioketone and during the partitioning of the peroxide intermediate. Steric interaction is suggested as the reason for variations in the product distribution between 1 and 2. Singlet oxygen is also generated through energy transfer from the triplet state of thioketones. These excited states also directly react with oxygen to yield ketone.

Original languageEnglish
Pages (from-to)127-131
Number of pages5
JournalJournal of Organic Chemistry
Volume47
Issue number1
StatePublished - Dec 1 1982
Externally publishedYes

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Ketones
Singlet Oxygen
Oxygen
Oxidation
Peroxides
Excited states
Energy transfer

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Oxidations of thioketones by singlet and triplet oxygen. / Jayathirtha Rao, V.; Muthuramu, K.; Ramamurthy, Vaidhyanathan.

In: Journal of Organic Chemistry, Vol. 47, No. 1, 01.12.1982, p. 127-131.

Research output: Contribution to journalArticle

Jayathirtha Rao, V, Muthuramu, K & Ramamurthy, V 1982, 'Oxidations of thioketones by singlet and triplet oxygen', Journal of Organic Chemistry, vol. 47, no. 1, pp. 127-131.
Jayathirtha Rao, V. ; Muthuramu, K. ; Ramamurthy, Vaidhyanathan. / Oxidations of thioketones by singlet and triplet oxygen. In: Journal of Organic Chemistry. 1982 ; Vol. 47, No. 1. pp. 127-131.
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