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Synlett 2000; 2000(3): 382-384
DOI: 10.1055/s-2000-6535
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Observations on the Use of Triphenylphosphonium Bromide as a Mild and Quantifiable Source of Hydrogen Bromide for Chemoselective Ring Opening of Epoxides to Bromohydrins

Carlos A. M. Afonso* , Nuno M. L. Vieira, William B. Motherwell
  • *Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa, Departamento de Quimica, Quinta da Torre, P-2825 Monte de Caparica, Portugal
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Publication Date:
31 December 2000 (online)

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The chemoselective ring opening of epoxides to bromohydrins in the presence of ketal, benzyloxymethoxy and trimethylsilyl ether functionality using triphenylphosphonium bromide is described. The preparation of a polymer supported variant is also reported.

triphenylphosphonium bromide - epoxide ring opening - bromohydrins