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AbstvactThe acid-catalysed rearrangements of fvans-and cis-4,5-epoxyhexan-1-01s and 5,6-epoxyheptan-1-01s demonstrate a preference for cyclic ether formation: tetrahydrofuran > tetrahydropyran > oxepan. The ether products arise by intramolecular hydroxyl displacement of the epoxide oxygen with inversion of configuration. Reactions of trans-and cis-epoxypentan-1-01s give a mixture of tvans-and cis-2-methyl-tetrahydrofuran-3-01s (8) and (9). From each epoxide one methyltetrahydrofuranol must arise by nucleophilic displacement of the secondary epoxide oxygen with retention of configuration.

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