Abstract
Abstract Unstable dimethylsulfonium (phenylthio)methylide (2) is prepared in a THF solution from the corresponding sulfonium salt by treating it with n-butyllithium. Sulfenyl-substituted stable phenacylides 6a and 6b are obtained in three ways. The ylide 6a decomposes at 120°C in benzene to give (E)-9, the dimer of benzoyl(phenylthio)carbene. In contrast, the heating of 6a in ethanol affords ethanolysis products (11, 12) and ethyl benzoate. The alkylation of 6a and 6b with trimethyl- and triethyloxonium fluoroborate gives the vinylsulfonium salt 13. The ylide 2 reacts with (Z)- and (E)-1,2-dibenzoylethylene and with diethyl fumarate to give cyclopropanes, 15 and 16 respectively.
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