Oxygen transfer from sulfoxides

Oxidation of alkylarenes catalyzed by a polyoxomolybdate, [PMo12O40]3-

Alexander M. Khenkin, Ronny Neumann

Research output: Contribution to journalArticle

103 Citations (Scopus)

Abstract

The polyoxomolydate of the Keggin structure, PMo12O40 3-, catalyzes, under anaerobic conditions, oxygen transfer from sulfoxides to alkylarenes such as xanthene and diphenylmethane to yield xanthen-9-one and benzophenone, respectively. With use of 17O and 18O labeled phenylmethylsulfoxide it was shown that the sulfoxide is complexed by the polyoxometalate and the oxygen is transferred from the sulfoxide to the alkylarene. There is a good correlation between the reaction rate and the heterolytic benzylic C-H bond energy indicating a hydride transfer reaction from the alkylarene to the polyoxometalate-sulfoxide complex. In the case of triphenylmethane the resulting carbocation reacts to yield 9-phenylfluorene as the major product. The reaction kinetics supports such a reaction pathway.

Original languageEnglish
Pages (from-to)4198-4199
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number16
DOIs
Publication statusPublished - Apr 24 2002

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sulfoxide
Sulfoxides
Xanthenes
Oxygen
Oxidation
Catalyst supports
Hydrides
Reaction kinetics
Reaction rates
Hydrogen
(PMo12O40)3-

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Oxygen transfer from sulfoxides : Oxidation of alkylarenes catalyzed by a polyoxomolybdate, [PMo12O40]3-. / Khenkin, Alexander M.; Neumann, Ronny.

In: Journal of the American Chemical Society, Vol. 124, No. 16, 24.04.2002, p. 4198-4199.

Research output: Contribution to journalArticle

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