Facile and selective procedure for the synthesis of bridged 1,2,4,5-tetraoxanes; strong acids as cosolvents and catalysts for addition of hydrogen peroxide to beta-diketones

J Org Chem. 2009 May 1;74(9):3335-40. doi: 10.1021/jo900226b.

Abstract

A facile, experimentally simple, and selective method was developed for the synthesis of bridged 1,2,4,5-tetraoxanes based on the reaction of hydrogen peroxide with beta-diketones catalyzed by strong acids (H(2)SO(4), HClO(4), HBF(4), or BF(3)). The yields of the target products vary from 44% to 77%. 1,2,4,5-Tetraoxanes can easily be separated from other reaction products by column chromatography. A high concentration of a strong acid is a key factor determining the selectivity of formation and the yield of 1,2,4,5-tetraoxanes. Unlike many compounds containing the O-O bond, which undergo rearrangements in acidic media, the resulting cyclic peroxides are quite stable under these conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Catalysis
  • Hydrogen Peroxide / chemistry*
  • Ketones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Solvents / chemistry*
  • Substrate Specificity
  • Tetraoxanes / chemical synthesis*
  • Tetraoxanes / chemistry
  • X-Ray Diffraction

Substances

  • Acids
  • Ketones
  • Solvents
  • Tetraoxanes
  • Hydrogen Peroxide