Acid-catalysed rearrangements of trans- and cis-1-acetoxy-3,4-epoxypentane and 1-acetoxy-4,5-epoxyhexane
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 8,p. 261-262
- https://doi.org/10.1039/c39730000261
Abstract
Acid-catalysed rearrangement of trans- and cis-1-acetoxy-3,4-cpoxypentanes and 1-acetoxy-4,5-epoxyhexanes give cis- and trans-2-methyl-3-acetoxytetrahydrofuran and threo- and erythro-2-(1-acetoxyethyl)tetrahydrofuran respectively with retention of configuration at the epoxide carbon atoms; the mechanism is consistent with the intermediary of orthoesters.Keywords
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