Investigations on reactions of cyclene α-oxides

The influence of the reaction conditions on the order of addition of alcohols and α-chloro ethers in an acid medium to dioxides of 1-vinyl-3-cyclohexene is described on the basis of a determination of the percentage content of the ratio of the isomers by IR spectroscopy. It has been established that under mild conditions the addition takes place selectively with the predominant opening of the oxide ring attached to the six-membered carbon ring. More severe conditions (higher temperature, smaller amount of solvent) favor the formation of isomers with an opened oxide ring on the ethylene grouping.