Abstract
Abstract Treatment of 9-thiaphenanthrenium salt 1 with conjugated dienes underwent regio- and stereospecific [2++4]-type polar cycloaddition to afford the corresponding sulfonium salt adducts 2 in good yields. Nucleophilic attack of some alcohols to the cycloadduct 2a led to the two kinds of ring-opened compounds 3 and 4. Reactions of compound 2a with a variety of bases yielded the vinylcyclopropane derivative 5 and the ring-opened product 6. Treatment of compound 2a with LDA in the presence of methyl acrylate afforded the compound 7 which is believed to derive from Michael-addition of a reactive ylide intermediate to an α,β-unsaturated ester. Reductive cleavage of compound 2a with NaBH4 or SmI2 afforded the ring-opened product 8.
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