Über eine ungewöhnliche Cyclisationsreaktion bei der Umsetzung von (+)‐Epoxy‐α‐dihydrojonon mit Hydrazinhydrat

Abstract

Abstract (+)‐Epoxy‐α‐dihydroionone ( 2 ) is formed completely stereospecifically from (+)‐α‐ionone ( 1 ). Under the conditions of the Wharton reaction this epoxide gives the expected isomeric allyl alcohols 4 and 5 and, surprisingly, the bicyclic allyl alcohol 3 . The structure and absolute configuration of the reaction products have been established. A common intermediate for the formation of compounds 3, 4 and 5 is probably the vinyl anion C.