In the slow stage of the acid-catalysed ring-opening of steroidal 5,6-epoxides in ethyl methyl ketone containing a little water, breaking of the O–C-6 bond is thought to be appreciably advanced before the protonated epoxide is attacked by the incoming nucleophile.
J. M. Diggle, M. D. Halliday, G. D. Meakins and M. S. Saltmarsh, J. Chem. Soc. D, 1969, 819 DOI: 10.1039/C29690000819
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