Experimental and quantum-chemical study of the interaction of cyclohexanediones and their monoethylene ketals with hydrogen peroxide

  • E. K. Starostin
  • A. A. Mazurchik
  • A. V. Ignatenko
  • V. M. Promyslov
  • N. D. Chuvylkin
  • G. I. Nikitin
Organic Chemistry Reactivity
  • 31 Downloads

Abstract

The reactivity of cyclohexanediones and their monoethylene ketals with hydrogen peroxide was studied. It was established that 1,2- and 1,3-cyclohexanediones virtually do not react with H2O2, whereas 1,4-cyclohexanedione forms 1,4-dihydroxy-1,4-dihydroperoxycyclohexane. Monoethylene ketals of cyclohexanediones react with hydrogen peroxide to form the corresponding α-hydroxy-α-hydroperoxides. The stereoelectronic factors determining the difference in reactivity of the carbonyl fragment in cyclohexanone, 1,2-cyclohexanedione, and its monoethylene ketal were analyzed within the framework of the semiempirical quantum chemical method MNDO.

Keywords

cyclohexanediones monoketals hydrogen peroxide peroxide structure quantum-chemical calculations 

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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • E. K. Starostin
  • A. A. Mazurchik
  • A. V. Ignatenko
  • V. M. Promyslov
  • N. D. Chuvylkin
  • G. I. Nikitin

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