Studies in the field of reactions of cyclene <Emphasis Type="Italic">α</Emphasis>-oxides

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.