The acetolysis of 1-acetyl-1,2-epoxycyclohexane (IV) with glacial acetic acid gives the trans diol monoacetate (V).
A study was made of the stabilities of the isomeric acetylcyclohexanediols (II) and (III) under alkaline and acid conditions. Under alkaline conditions the trans acetylcyclohexanediol (II) and its monoacetate (V) are converted into the cis acetylcyclohexanediol (III). Under these conditions the latter is not isomerized into the trans isomer.
Some observations are made relating to the possible causes of the different behaviors of substances of the trans and cis series in acetylation and reactions leading to carbonyl derivatives.
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This article is published in accordance with a resolution of the Conference of Chief Editors of Journals of the Academy of Sciences of the USSR of June 12, 1962, as a dissertation paper by A. M. Moiseenko.
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Moiseenko, A.M., Akhrem, A.A. Corticosteroid analogs. Russ Chem Bull 12, 967–972 (1963). https://doi.org/10.1007/BF00845474
- Acetic Acid