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Chemistry of Heterocyclic Compounds

, Volume 4, Issue 4, pp 425–426 | Cite as

Studies in the field of reactions of cyclene α-oxides

IV. Reaction of 1-methylcyclopentene oxide with alcohols
  • L. A. Mukhamedova
  • M. I. Kudryavtseva
Article
  • 28 Downloads

Abstract

The reaction of 1-methylcyclopentene oxide with alcohols (methanol, ethanol, n-propanol and isopropanol, n-butanol, and n-pentanol) in the presence of Na and of BF3 etherate has been described. The addition of alcohols in an alkaline medium takes place with the formation of secondary ethers of 1-methylcyclopentane-1,2-diol. In an acid medium, tertiary ethers of 1-methylcyclopentane-1,2-diol possibly contaminated with the secondary ethers are formed. In an acid medium, not only does addition take place but the initial oxide isomerizes into a carbonyl compound and to some extent forms trans-1-methylcyclopentane-1,2-diol. With isopropanol, in an alkaline medium the initial oxide is recovered and in an acid medium only the isomerization product is formed.

Keywords

Oxide Alcohol Ether Methanol Carbonyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • L. A. Mukhamedova
    • 1
  • M. I. Kudryavtseva
    • 1
  1. 1.Arbuzov Institute of Organic and Physical ChemistryAS USSRKazan

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