1,4-Addition of azide to trans-diepoxycyclopentane with solvent participation

Article abstract of DOI:10.1016/S0040-4020(01)80582-2

The reaction of trans-diepoxycyclopentane with azide leads in methanol to the expected azidohydrins; a 1,4-adduct with a 'central' epoxy group is also formed. When the reaction is carried out in acetone/water 1:1, an additional product, which is the acetonide of an azido-trihydoxycyclopentane, is observed. This compound must have been formed by participation of the solvent followed by cyclization.