1,2- and 3,4-Epoxy-1,2,3,4-tetrahydrophenanthrene were each separable into enantiomers while the corresponding 1,2- and 3,4-epoxydihydrophenanthrene (derived from identical chiral precursors) showed evidence of spontaneous racemization; preliminary PMO calculations indicate that oxepin intermediates could account for this configurational instability.
D. R. Boyd, J. D. Neill and M. E. Stubbs, J. Chem. Soc., Chem. Commun., 1977, 873 DOI: 10.1039/C39770000873
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