Synlett 2007(4): 0664-0665  
DOI: 10.1055/s-2007-967956
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

m-Chloroperoxybenzoic Acid (MCPBA)

Rekha Tank*
Synthetic Chemistry Division, Defence Research and Development Establishment, Gwalior 474002 India
e-Mail: eakta@rediffmail.com;
Further Information

Publication History

Publication Date:
21 February 2007 (online)

Introduction

MCPBA is a strong electrophilic oxidising agent. It is a white powder (mp 90 °C), easy to handle, flammable, ­hygroscopic, soluble in less-polar solvents like CH2Cl2, CHCl3, 1,2-DCE, EtOAc, EtOH, t-BuOH, Et2O and some nonpolar solvents like benzene, it is slightly soluble in hexane, CCl4 and insoluble in H2O. Pure MCPBA is shock-sensitive and can deflagrate, it is potentially explosive beyond 85% purity. It shows 1% degradation per year at room temperature. It is widely used in organic chemistry to carry out a variety of chemical transformations such as oxidation of carbonyl compounds, iminoindolines, olefins, imines, alkanes, silyl enol ethers, N- and S-hetero­cycles, active methylene groups, fluoromethylated allylic bromides, cyclic acetals and N-substituted phthal­imidines, etc. [1a] Besides these it also oxidises selenides, furans and phosphates to selenoxides, pyranones and phosphates, respectively. It is superior to H2O2 and other oxidising agents because of its reactivity, stereoselec­tivity, purity and yield of products. [1b]

    References

  • 1a Encyclopedia of Reagents for Organic Synthesis   Vol. 2:  Paquette LA. Wiley; Chichester: 1995.  p.1192 
  • 1b International Electronic Conference on Synthetic Organic Chemistry, Sept. 2000.ungetaggter Text Ende
  • 2 Anon., Chem. Week  1963,  92:  55 
  • 3 Kobayashi S. Tanaka H. Amii H. Uneyama K. Tetrahedron  2003,  59:  1547 
  • 4 Burford N. Dyker C. Lumsden M. Decken A. Angew. Chem. Int. Ed.  2005,  44:  6193 
  • 5 Shulpin G. Evans H. Mandelli D. Kozlov Y. Vallina T. Woitiski C. Jimenez R. Carvalho W. J. Mol. Catal. A: Chem.  2004,  219:  255 
  • 6 Santos R. Brocksom T. Zanotto R. Brocksom U. Molecules  2002,  7:  129 
  • 7 Kim J. Rhee H. Kim M. J. Korean Chem. Soc.  2002,  46:  479 
  • 8 An G. Kim M. Kim J. Rhee H. Tetrahedron Lett.  2003,  44:  2183 
  • 9 Chang M. Pai C. Lin C. Tetrahedron Lett.  2006,  47:  3641 
  • 10 Han H. Kim M. Son J. Jeong I. Tetrahedron Lett.  2006,  47:  209