Oxygen transfer from sulfoxides: Oxidation of alkylarenes catalyzed by a polyoxomolybdate, [PMo12O40]3-

Alexander M. Khenkin, Ronny Neumann

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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
Issue number16
Publication statusPublished - Apr 24 2002


ASJC Scopus subject areas

  • Chemistry(all)

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