Chemistry of Heterocyclic Compounds

, Volume 18, Issue 10, pp 1008–1011 | Cite as

Chemistry of oxalyl derivatives of methyl ketones. 28. Reaction of carbonyl compounds of adamantane with 5-phenyl-2,3--dihydrofuran-2,3-dione

  • Yu. S. Andreichikov
  • M. P. Sivkova
  • N. N. Shapet'ko


The reaction of substituted methyl 1-adamantyl ketones with an equimolar amount of 5-phenyl-2,3-dihydrofuran-2,3-dione under the conditions of the thermal decarbonylation of the latter leads to the corresponding 2-methyl-2-adamantyl-6-pheny1-1,3-dioxen-4-ones, 6-phenyl-3-benzoyl-2,4-dione, and the starting ketones. The steric and electronic factors that affect the yields of the dioxen-4-ones were examined. α-Hydroxymethyl 1-adamantyl ketones open up the furan ring to give 1-adamantoylmethyl benzoylpyruvate. Data from the IR, PMR, and UV spectra are presented.


Carbonyl Ketone Dione Furan Carbonyl Compound 
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Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • Yu. S. Andreichikov
    • 1
  • M. P. Sivkova
    • 1
  • N. N. Shapet'ko
    • 1
  1. 1.Perm State Pharmaceutical InstitutePerm

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