Abstract
The acid-catalysed rearrangements of trans- and cis-4,5-epoxyhexan-1- ols and 5,6-epoxyheptan-1-ols 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-ols give a mixture of trans- and cis-2-methyl-tetrahydro- furan-3-ols (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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