Electrophilic addition of 1 -[o- (phenylsulfanyl)phenyI] -2-(p-methoxypheny1)ethyne with electrophiles such as perchloric acid, tetrafluoroboric acid, bromine, and benzenesulfenyl chloride gave 1 -phenyl-I -benzothiophenium salts exclusively. The substituent effect on the intramolecular cyclization with electrophiles has been examined. The aryl-substituted alkynes afforded predominantly the cyclized 1 -phenyl-I -benzothiophenium salts but methyl-substituted alkynes yielded a mixture of the cyclized salt and the 1,2-addition product. In addition to the intramolecular cyclization at the intermediate vinyl cation or bridged ion, it is proposed, on the basis of the product from the reaction of methyl-substituted alkyne, that the 71 complex partly participates in the i n t ra m ol ec u I a r cyc I izat i o n .
Reaction of 1,2,3-triarylbenzo[b]thiophenium salts with alkoxide anions results in the exclusive formation of (2) alkoxy-substituted alkenes, indicating that the nucleophilic ring-opening reaction proceeds with complete retention of configuration.
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