A study of hydroxyl participation in acyclic epoxide systems. Acid-catalysed rearrangements of trans- and cis-3,4-Epoxypentan-1-ols, 4,5-Epoxyhexan-1-ols, and 5,6-Epoxyheptan-1-ols
- 1 January 1973
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 26 (11) , 2521-2526
- https://doi.org/10.1071/ch9732521
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.Keywords
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