The reaction of nitrosoarenes and 1 -(trimethylsilyl)vinylmagnesium bromide in dibutyl ether represents a useful tool for the synthesis of 2-(trimethylsilyl)indoles by cyclisation of benzene derivatives. The use of more common ethers as the solvent leads to large amounts of azo and azoxy derivatives. Conversely, the reaction of nitroarenes and 1-(trimethylsilyl)vinylmagnesium bromide gives conjugate addition products. The reasons for this behaviour are discussed.
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Journal of the Chemical Society, Perkin Transactions 1
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