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Microwave-Assisted Meyer–Schuster Rearrangement of Propargylic Alcohols Catalyzed by the Oxovanadate Complex [V(O)Cl(OEt)2]

  1. Prof. Dr. Antonio Antiñolo1,
  2. Dr. Fernando Carrillo-Hermosilla1,*,
  3. Dr. Victorio Cadierno2,
  4. Dr. Joaquín García-Álvarez2,*,
  5. Prof. Dr. Antonio Otero1

Article first published online: 6 OCT 2011

DOI: 10.1002/cctc.201100239

Issue

ChemCatChem

ChemCatChem

Volume 4, Issue 1, pages 123–128, January 2, 2012

Additional Information

How to Cite

Antiñolo, A., Carrillo-Hermosilla, F., Cadierno, V., García-Álvarez, J. and Otero, A. (2012), Microwave-Assisted Meyer–Schuster Rearrangement of Propargylic Alcohols Catalyzed by the Oxovanadate Complex [V(O)Cl(OEt)2]. ChemCatChem, 4: 123–128. doi: 10.1002/cctc.201100239

Author Information

  1. 1

    Departamento de Química Inorgánica, Orgánica y Bioquímica, Facultad de Ciencias Químicas, Campus de Ciudad Real, Universidad de Castilla-La Mancha, Campus Universitario, 13071 Ciudad Real (Spain), Fax: (+34) 926-295-318

  2. 2

    Departamento de Química Orgánica e Inorgánica, IUQOEM (Unidad asociada al CSIC), Universidad de Oviedo, Julián Claveria 8, 33006 Oviedo (Spain), Fax: (+34) 985-103-446

*Departamento de Química Inorgánica, Orgánica y Bioquímica, Facultad de Ciencias Químicas, Campus de Ciudad Real, Universidad de Castilla-La Mancha, Campus Universitario, 13071 Ciudad Real (Spain), Fax: (+34) 926-295-318

Publication History

  1. Issue published online: 27 DEC 2011
  2. Article first published online: 6 OCT 2011
  3. Manuscript Received: 18 JUL 2011

Funded by

  • Ministerio de Ciencia e Innovación (MICINN). Grant Numbers: CSD2007-00006, CTQ2008-00506/BQU, CTQ2010-14796/BQU, CTQ2009-09214/BQU
  • Junta de Comunidades de Castilla-La Mancha. Grant Number: PCI08–0032
  • MICINN
  • European Social Fund

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Keywords:

  • alcohols;
  • enals;
  • microwave chemistry;
  • sigmatropic rearrangement;
  • vanadium

Abstract

A general and efficient procedure for the selective Meyer–Schuster isomerization of both, terminal and internal alkynols, has been developed by using catalytic amounts of the readily accessible oxovanadium(V) complex [V(O)Cl(OEt)2]. Reactions proceeded smoothly in toluene at 80 °C under microwave irradiation to provide the corresponding α,β-unsaturated carbonyl compounds in excellent yields and short times without the assistance of any additive.

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