Triarylsulfonium bromides were synthesized by the reaction of diaryl sulfoxides with aryl Grignard reagents in the presence of TMSCl followed by treatment with HBr aqueous solution. Triarylsulfonium bromides bearing three identical substituents on sulfur atom were synthesized by the treatment of dimethyl sulfite or thionyl chloride with 5 equivalents of Grignard reagent in the presence of TMSCl.
On treatment of allyl-t-butyldiphenylsilane with t-BuOK and 18-Crown-6 in DMSO at room temperature, isomerization of the olefinic double bond and subsequent substitution of phenyl group with hydroxy group took place smoothly to afford alkenylsilanol derivatives in good yields.
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