Nitrogen oxides/selenium dioxide-mediated benzylic oxidations

Joseph E. Remias, Ayusman Sen

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The oxidation of benzylic groups to the corresponding carboxylic acid functionality by dioxygen is mediated by a combination of nitrogen oxides and selenium dioxide (SeO2). Substrates examined include alkylnaphthalenes and alkylpyridines. The aldehyde appears to be an intermediate in the reaction. Mechanistic studies suggest that the rate-determining step is hydrogen atom abstraction by nitrogen dioxide (NO2) to form the benzyl radical. Selenium dioxide subsequently oxidizes this radical to the desired product.

Original languageEnglish (US)
Pages (from-to)63-70
Number of pages8
JournalJournal of Molecular Catalysis A: Chemical
Volume201
Issue number1-2
DOIs
StatePublished - Jul 1 2003

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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