4.5 Article

Preparation of the First Bench-Stable Phenyl Selenolate: an Interesting On Water Nucleophilic Reagent

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 32, Pages 5387-5390

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800869

Keywords

Selenolate; Zinc; On water reactions; Epoxides; Nucleophiles

Funding

  1. M.I.U.R. (Ministero Italiano University e Ricerca)
  2. PRIN2005 (Progetto di Ricerca d'Interesse Nazionale)
  3. Consorzio CINMPIS
  4. Bari (Consorzio Interuniversitario Nazionale di Metodologie a Processi Innovativi di Sintesi)
  5. University of Perugia

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In this communication we report the synthesis and the characterization of the first solid and air-stable selenolates, starting from commercially available phenylselenenyl halides and elemental zinc. These reagents were efficiently employed in the ring opening of epoxides as well as in other nucleophilic substitution and addition reactions showing an unexpected rate acceleration in water suspension at room temperature. ( (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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