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Russian Chemical Bulletin

, Volume 59, Issue 10, pp 1930–1936 | Cite as

Oxidative and hydrolytic cleavage of cyclopropane and spirocyclobutane derivatives of 6,8-dioxabicyclo[3.2.1]octane, the products of transformation of levoglucosenone

  • R. A. Novikov
  • R. R. Rafikov
  • E. V. Shulishov
  • Yu. V. Tomilov
Full Articles
  • 113 Downloads

Abstract

A new method for the synthesis of (1R,4S,5S)-4-hydroxymethyl-3-oxabicyclo[3.1.0]hexan2-one, the cyclopropane analog of (S)-5-hydroxypent-2-en-4-olide, has been suggested based on oxidation of (1S,2S,4R,6R)-7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one. Oxidation of cyclobutanones, spirojoined with the fragments of 6,8-dioxabicyclo[3.2.1]oct-2-ene, 6,8-dioxabicyclo[3.2.1]octane (at position 4), or 7,9-dioxatricyclo[4.2.1.02,4]nonane (at position 5), upon the action of m-chloroperoxybenzoic acid or the KMnO4-H2SO4-H2O system leads to the corresponding spirojoined butanolides in 73–85% yields. The same cyclobutanones easily undergo the four-membered ring opening upon the action of dilute H2SO4 at 50–90 °C to form 6,8-dioxabicyclo[3.2.1]octane-4- or 7,9-dioxatricyclo[4.2.1.02,4]nonane-5-propionic acid.

Key words

7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one 3-oxabicyclo[3.1.0]hexan-2-ones spiro{6,8-dioxabicyclo[3.2.1]octane-4,2′-cyclobutanones} spiro compounds γ-lactones oxidation hydration cyclobutanones levoglucosenone 

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Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  • R. A. Novikov
    • 1
  • R. R. Rafikov
    • 1
  • E. V. Shulishov
    • 1
  • Yu. V. Tomilov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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