Oxidation of Hydrocarbons by Aqueous Platinum Salts: Mechanism and Selectivity

Jay A. Labinger, Andrew M. Herring, David K. Lyon, Gerrit A. Luinstra, John E. Bercaw, István T. Horváth, Karsten Eller

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Abstract

Water-soluble organic compounds are selectively oxidized by aqueous solutions of chloroplatinum(II) and chloroplatinum(IV) salts. p-Toluenesulfonic acid undergoes stepwise hydroxylation to the corresponding alcohol and aldehyde, with no further oxidation to the carboxylic acid; p-ethylbenzenesulfonic acid is functionalized at both the benzylic and methyl positions. Ethanol is converted to a spectrum of C2 (chloro)oxygenates, including ethylene glycol and 2-chloroethanol, products resulting from methyl functionalization. n-Propanol is also significantly attacked at the methyl position. 13C labeling and kinetics studies were used to elucidate mechanistic pathways. The reactivity of a methyl group CH bond is at least as high as that of a CH bond α to oxygen, in contrast to most alkane conversion systems.

Original languageEnglish
Pages (from-to)895-905
Number of pages11
JournalOrganometallics
Volume12
Issue number3
DOIs
Publication statusPublished - Jan 1 1993

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Labinger, J. A., Herring, A. M., Lyon, D. K., Luinstra, G. A., Bercaw, J. E., Horváth, I. T., & Eller, K. (1993). Oxidation of Hydrocarbons by Aqueous Platinum Salts: Mechanism and Selectivity. Organometallics, 12(3), 895-905. https://doi.org/10.1021/om00027a045