Download PDF
Synlett 2009(1): 155-156  
DOI: 10.1055/s-0028-1083138
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Ozone: A Versatile Oxidizing Agent in Academic Syntheses and Industrial Processes

Giovanni Wilson Amarante*
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, CEP 13083-970, Campinas, São Paulo, Brasil.
e-Mail: amarante@iqm.unicamp.br;
Further Information

Publication History

Publication Date:
12 December 2008 (online)

   Permissions and Reprints All articles of this category

Introduction

Due to its simple preparation (O3 from O2) and efficiency, ozone has attracted the attention of academic and industrial sectors as an oxidizing agent, mainly for the clean and efficient oxidative cleavage of double bonds (ozono­lysis). [¹]

Ozone was discovered in 1847 by Schönbein who observed that ozone did not convert organic compounds to the highest oxidation level (CO2, H2O), but led them to intermediate oxidative levels such as carboxylic acids. Some years later, Harries demonstrated the high applicability of ozone in organic reactions, especially with double bond oxidations. [²]

Based on his own results and data available in the literature, Criegee has proposed a mechanism to explain oxidative cleavage during ozonolysis. According to Criegee, a molozonide and 1,2,4-trioxolane (ozonide) are the intermediates of this reaction. Experimental evidence confirmed this proposition and this mechanism is currently accepted (Scheme  [¹] ). [³]

Scheme 1 Mechanistic proposal for ozonolysis

The ozonide intermediate can afford ketones, aldehydes and alcohols after reductive workups, while oxidative conditions can furnish ketones or carboxylic acids.

Ozone has been applied to the development of new synthetic methodologies, [4] key intermediates in the total synthesis of natural and bioactive compounds [5] and new protocols in the pharmaceutical industries. [6]

    References

  • 1 Ornum SGV. Champeau RM. Pariza R. Chem. Rev.  2006,  106:  2990 
    CrossrefGoogle Scholar
  • 2 Rubin MB. Helv. Chim. Acta  2003,  86:  930 
    CrossrefGoogle Scholar
  • 3 Criegee R. Angew. Chem. Int. Ed. Engl.  1975,  14:  745 
    CrossrefGoogle Scholar
  • 4 Molander GA. Cooper DJ. J. Org. Chem.  2007,  72:  3558 
    CrossrefGoogle Scholar
  • 5a Bailey PS. Ozonation in Organic Chemistry   Vol. I:  Academic Press; New York: 1978. 
    Google Scholar
  • 5b Bailey PS. Ozonation in Organic Chemistry   Vol. II:  Academic Press; New York: 1982. 
    Google Scholar
  • 5c Frezza M. Soulère L. Queneau Y. Doutheau A. Tetrahedron Lett.  2005,  46:  6495 
    Google Scholar
  • 5d Abella CAM. Rezende P. De Souza MFL. Coelho F. Tetrahedron Lett.  2008,  49:  145 
    Google Scholar
  • 5e White JD. Johnson AT. J. Org. Chem.  1994,  59:  3347 
    Google Scholar
  • 6a Chai D. Genders D. Weinberg N. Zappi G. Bernasconi E. Lee J. Roletto J. Sogli L. Walker D. Martin RC. Menon V. Zelenay P. Zhang H. Org. Process Rev. Dev.  2002,  6:  178; and references cited therein 
    Google Scholar
  • 6b Cabaj JE. Kairys D. Benson TR. Org. Process Res. Dev.  2007,  11:  378 
    Google Scholar
  • 6c Bandini M. Cozzi PG. de Angelis M. Umani-Ronchi A. Tetrahedron Lett.  2000,  41:  1601 
    Google Scholar
  • 7 Molander GA. Ellis NM. Acc. Chem. Res.  2007,  40:  275 
    CrossrefPubMedGoogle Scholar
  • 8 Pearlman BA. Padilla AG. Hach JT. Havens JL. Pillai MD. Org. Lett.  2006,  8:  2111 
    CrossrefGoogle Scholar
  • 9a Clark RD. Heathcock CH. Tetrahedron Lett.  1974,  15:  2027 
    Google Scholar
  • 9b Clark RD. Heathcock CH. J. Org. Chem.  1976,  41:  1396 
    Google Scholar
  • 10 Avery MA. Chong WKM. Jennings-White C. J. Am. Chem. Soc.  1992,  114:  974 
    CrossrefGoogle Scholar
  • 11 Ragan JA. am Ende DJ. Brenek SJ. Eisenbreis SA. Singer RA. Tickner DL. Teixeira JJ. Vanderplas BC. Weston N. Org. Process Res. Dev.  2003,  7:  155 
    CrossrefGoogle Scholar