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Issue 11, 1991
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Reactivity of nitro- and nitroso-arenes with vinyl grignard reagents: synthesis of 2-(trimethylsilyl)indoles

Abstract

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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Article type: Paper
DOI: 10.1039/P19910002757
Citation: J. Chem. Soc., Perkin Trans. 1, 1991,0, 2757-2761
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    Reactivity of nitro- and nitroso-arenes with vinyl grignard reagents: synthesis of 2-(trimethylsilyl)indoles

    G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri and E. Marcantoni, J. Chem. Soc., Perkin Trans. 1, 1991, 0, 2757
    DOI: 10.1039/P19910002757

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