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Synlett 1996; 1996(8): 783-784
DOI: 10.1055/s-1996-5530
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Variable Chemo-selective Electrophilic Attack on Silylated Aromatic Aldehydes

Paulo R. R. Costa1 , Alcides J. M. da Silva1 , Mário L. A. A. Vasconcellos1 , Cláudio C. Lopes2 , Rosangela S. C. Lopes2
  • 1Laboratório de Síntese Orgânica I, UFRJ, Núcleo de Pesquisas de Produtos Naturais, Bloco H, CCS, 21941-580, RJ, Brazil
  • 2Departamento de Química Analítica, Instituto de Química, UFRJ, CT, Bloco A, 21949-900, RJ, Brazil
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Publication History

Publication Date:
31 December 2000 (online)

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The ortho-aryltrimethylsilane aldehyde derivatives 1a-c and 2a-c were prepared from the corresponding alkoxylated aromatic aldehydes using an ortho-lithiation strategy. Bromination led to clean substitution of the trimethylsilane whereas nitration and acetylation sometimes give substitution of a proton and sometimes of the silane.

lithiation - ortho-aryltrimethylsilane aldehydes - bromination - nitration - acetylation