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Studies in the field of reactions of cyclene α-oxides

IV. Reaction of 1-methylcyclopentene oxide with alcohols

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, AS USSR, Kazan

    L. A. Mukhamedova & M. I. Kudryavtseva

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  1. L. A. Mukhamedova
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  2. M. I. Kudryavtseva
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For part III, see [1].

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Mukhamedova, L.A., Kudryavtseva, M.I. Studies in the field of reactions of cyclene α-oxides. Chem Heterocycl Compd 4, 425–426 (1971). https://doi.org/10.1007/BF00486745

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  • DOI: https://doi.org/10.1007/BF00486745

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