Synlett 2005(12): 1962-1963  
DOI: 10.1055/s-2005-871968
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Urea-Hydrogen Peroxide Complex

Sandra Taliansky*
Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
e-Mail: staliansky@iqm.csic.es;
Further Information

Publication History

Publication Date:
20 July 2005 (online)

Introduction

The hydrogen bonded urea-hydrogen peroxide complex [CO(NH2)2·H2O2, UHP] is a cheap and commercially available white crystalline solid (mp 84-86 °C, dec.) obtained by recrystallization of urea from commercially available 33% aqueous hydrogen peroxide. [1]

Its stability at room temperature, high hydrogen peroxide content (36.2%) and the potential for releasing it in a controlled manner, [2] as well as its solubility in organic solvents (alcohols, dichloromethane) makes it a good and safe sub­stitute for anhydrous hydrogen peroxide (not available anymore) in most oxidation reactions.

UHP has been used for the epoxidation of a wide range of alkenes. [3] It is capable of oxidizing a number of functional groups: nitriles to amides, [4] oximes to nitroalkanes, [5] sulfides to sulfoxides [6] or sulfones, [7] aldehydes to acids, [8] etc. UHP has also been found useful for heteroatom oxidation reactions, [9] as well as to carry out Baeyer-Villiger [10] and related reactions. In recent years, UHP has proved to be effective in solid state reactions, both under heating [11] or microwave irradiation, [12] so becoming an interesting eco-friendly reagent.

    References

  • 1 Lu C.-S. Hughes EW. Giguère PA. J. Am. Chem. Soc.  1941,  63:  1507 
  • 2 Gonsalves AMR. Johnstone RAW. Pereira MM. Shaw J. J. Chem Res., Synop.  1991,  208 
  • 3a Cooper MS. Heaney H. Newbold AJ. Sanderson WR. Synlett  1990,  533 
  • 3b Fan CL. Lee WD. Teng NW. Sun YC. Chen K. J. Org. Chem.  2003,  68:  9816 
  • 3c Marigo M. Jranzén J. Toulsen TB. Whuang W. KøØgensen KA. J. Am. Chem. Soc.  2005,  127:  6964 
  • 4 Balicki R. Synth. Commun.  1993,  23:  3149 
  • 5 Ballini R. Marcantoni E. Petrini M. Tetrahedron Lett.  1992,  33:  4835 
  • 6 Gunaratne HQN. McKervey MA. Feutren S. Finlay J. Boyd J. Tetrahedron Lett.  1998,  39:  5655 
  • 7 Balicki R. Synth. Commun.  1999,  29:  2235 
  • 8 Heaney H. Newbold AJ. Tetrahedron Lett.  2001,  42:  6607 
  • 9 Heaney H. Aldrichimica Acta  1993,  26:  35 
  • 10 Astudillo L. Galindo A. González AG. Mansilla H. Heterocycles  1993,  36:  1075 
  • 11 Varma RS. Naicker KP. Org. Lett.  1999,  1:  189 
  • 12 Paul S. Nanda P. Gupta R. Synlett  2004,  531 
  • 13 Ghiron C. Nannetti L. Taddei M. Tetrahedron Lett.  2005,  46:  1643 
  • 14 Valderrama JA. González MF. Torres C. Heterocycles  2003,  60:  2343 
  • 15 Schofield LJ. Kerton OJ. McMorn P. Belthell D. Ellwood S. Hutchings GJ. J. Chem. Soc., Perkin Trans. 2  2002,  2064 
  • 16 Schofield LJ. Kerton OJ. McMorn P. Belthell D. Ellwood S. Hutchings GJ. J. Chem. Soc., Perkin Trans. 2  2002,  1475 
  • 17a Soldaini G. Synlett  2004,  1849 
  • 17b Goti A. Cardona F. Soldaini G. Org. Synth.  2005,  81:  204 
  • 18 Abu-Omar MM. Owens GS. Durazo A. In Ionic Liquids as Green Solvents   856:  Rogers RD. Seddon KR. ACS Symposium Series; 2003.  p.277 
  • 19a Boehlow TR. Spilling CD. Tetrahedron Lett.  1996,  37:  2717 
  • 19b Baldwin SW. Long A. Org. Lett.  2004,  6:  1653 
  • 20 Musumeci D. Sica D. Steroids  2002,  67:  661 
  • 21 Stankoviæ S. Espenson JH. J. Org. Chem.  2000,  65:  5528 
  • 22 Raj NKK. Ramaswamy AV. Manikandan P. J. Mol. Catal. A: Chem.  2005,  227:  37 
  • 23 Sasaki Y. Ushimaru K. Iteya K. Nakayama H. Yamaguchi S. Ichihara J. Tetrahedron Lett.  2004,  45:  9513 
  • 24 Shul’pin GB. Süss-Fink G. J. Chem. Soc., Perkin Trans. 2  1995,  1459 
  • 25 Jones CW. Hackett A. Pattinson I. Johnstone A. Wilson SL. J. Chem. Res., Synop.  1996,  438 
  • 26 Moody CJ. O’Connell JL. Chem. Commun.  2000,  1311 
  • 27 Lulinski P. Kryska A. Sosnowski M. Skulski L. Synthesis  2004,  441 
  • 28 Zielinska A. Skulski L. Tetrahedron Lett.  2004,  45:  1087