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The [8+2]-cycloaddition reaction can provide a straight-forward approach for the synthesis of 10-membered ring compounds.In this study,a formal [8+2] cycloaddition reaction of vinylphenylfuran and DMAD in three different systems,forming a variety of polycyclic compounds,have been reported.Both experimental and computational studies were applied to understand the potential reaction mechanism.It is supposed that the reaction proceeded through a tandem reactions of Diels-Alder/electrocyclization/[1,3]-H shift/retro-Diels-Alder.An important diradical but not an initially proposed o-quinodimethane was believed as the key intermediate in the reaction pathway.