Abstract
2-(4-Hydroxyalkyl)-1,3-dioxolanes (3a/3b, 5–7) undergo an acid-catalyzed rearrangement to give 2-hydroxyethyl alkanoic esters 8–11. The postulated mechanism, proceeding via the benzylic carbenium ion B and the 1,3-dioxolan-2-ylium cation C, is supported by the stereochemistry of the reaction and the results of deuterium labeling experiments.
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