電解酸化系における疎水性反応場を用いた付加環化反応

抄録

Unstable intermediates were generated in situ by electrochemical oxidation of phenolic compounds to give varied cycloadducts with dienes or alkenes by using hydrophobic fields in the reaction system. In an aqueous medium, Diels-Alder reactions of quinones and dienes were markedly prometed in the presence of sodium dodecylsulfate (SDS). Electrochemical generation of unstable quinones and subsequent cycloaddition reactions with varied dienes were mediated by SDS micelle. These electrolytic reactions were also accomplished in a conductive lithium perchlorate/nitromethane system in which Diels-Alder reactions were highly promoted. In this non-aqueous reaction system, electrochemical generation and cycloaddition reactions of ο-quinone methides and unactivated alkenes were also successful to give chroman and spirochroman skeletons which have been proven to be difficult to yield in usual methods. The electrolysis in the lithium perchlorate/nitromethane system was further applied to the proposed biomimetic cycloaddition of ο-quinone methides and terpenes to give natural euglobal skeletons.