A further selective pathway in thermal conversion of 2,5-epidioxy-2-alkoxy-2,5-dihydrofurans (2-alkoxyfuran endo-peroxides). Synthesis of the first 5-hydroperoxyfuran-2(5H)-ones

Abstract

Thermal conversion of the epidioxydihydrofurans 1 leads, via dioxetanes 3, to the stereoisomeric dimers 4 which have a structural relationship with antitumour cyclic peroxides and represent convenient starting materials for several multifunctional compounds; their mild acid hydrolysis provides a convenient entry to the synthesis of the furanone derivatives 7 and 8 which are structurally related to biologically active products.