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.
J. A. Donnelly, J. G. Hoey, S. O'Brien and J. O'Grady, J. Chem. Soc., Perkin Trans. 1, 1973, 2030 DOI: 10.1039/P19730002030
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