Rearrangement of cyclopropyl epoxides to 3,6-dihydro-2H-pyrans
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2030-2033
- https://doi.org/10.1039/p19730002030
Abstract
Aryl-substituted cyclopropyl epoxides rearrange to 3.6-dihydro-2H-pyrans. This new rearrangement is related to that of vinyl epoxides to dihydrofurans but occurs under much milder conditions, probably by way of a homoallyl cation resulting from opening of the epoxide ring by adventitious acid catalysis. It provides a relatively simple procedure for the synthesis of 2-aryl-3,6-dihydro-2H-pyrans.Keywords
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