Tertiary amine oxidation using HOF-CH3CN: A novel synthesis of N-oxides

Sharon Dayan, Kol Moshe, Shlomo Rozen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

HOF·CH3CN, probably the best oxygen transfer agent organic chemistry has to offer, is easily made by bubbling diluted fluorine (10-15%) through aqueous acetonitrile solution. Used as formed without any isolation or purification, it reacts with various tertiary amines such as pyridine derivatives, polyaromatic nitrogen containing compounds and aliphatic and alicyclic ones to form the corresponding N-oxides. When two nitrogen atoms are present it is possible to make both the N-monoxides and the N,N-dioxides. The reaction times are short (a few minutes), conditions are very mild (0-25 °C) and the yields range from good to excellent (70-95%).

Original languageEnglish
Pages (from-to)1427-1430
Number of pages4
JournalSynthesis
Issue numberSPEC. ISS.
DOIs
StatePublished - 1999

Keywords

  • N-oxides
  • Oxidation
  • Tertiary amines

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