The hydrolysis of α,α'‐dimethoxydihydrofurans

A series of α,α ‐dimethoxydihydrofurans have been prepared and subjected to various acidic and neutral hydrolysis conditions in attempts to prepare conjugated enediones in a stereospecific manner. Isomerization of the 3‐hexene‐2,5‐diones and rearrangements of other enediones to β,γ‐unsaturated‐γ‐lactones have been uncovered. Methods of assignment of stereochemical configuration to the enediones are evaluated; reaction with hydrazine hydrate in the absence of acid is proposed as a useful criterion.