Synthesis of epoxy dinitriles from citral and their acid-catalyzed transformations

Abstract
2,3-and 6,7-Epoxy derivatives of citral react with malononitrile in the presence of basic Csβ-zeolite to give the corresponding epoxyalkenylidenemalononitriles as the major products. Epoxy dinitriles obtained from 6,7-epoxycitral undergo acid-catalyzed transformations into tetrahydrofuran derivatives or acyclic polyenes containing hydroxy and cyano groups, depending on the catalyst nature.