Synlett 2009(2): 328-329  
DOI: 10.1055/s-0028-1087527
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Burgess Reagent: From Oblivion to Renaissance in Organic Synthesis

Soumava Santra*
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202.
e-Mail: soumava@chem.wayne.edu;
Further Information

Publication History

Publication Date:
15 January 2009 (online)

Introduction

In 1968, E. M. Burgess discovered that methyl N-(triethyl­ammoniumsulphonyl) carbamate salt (1), [¹] commonly known as the Burgess reagent, could be used as a mild and selective dehydrating agent [²] for the conversion of secondary and tertiary alcohols into alkenes. The dehydration occurs through an internal elimination (E i ) mechanism resulting in syn-elimination. In recent years there has been a revival of interest in the Burgess reagent [³] due to its versatility in synthetically useful transformations that have facilitated functional group conversions. The ­reagent is highly soluble in most common organic solvents including those that are non-polar. The most noteworthy application has been in the cyclodehydration of hydroxy amides and thioamides to afford corresponding heterocycles. Because of the mild conditions as well as high selectivity, the reagent has received wide acceptance in the area of synthetic chemistry.

Scheme 1 Preparation of the Burgess reagent.

    References

  • 1 Atkins GM. Burgess EM. J. Am. Chem. Soc.  1968,  90:  4744 
  • 2 Burgess EM. Penton HR. Taylor EA. J. Org. Chem.  1973,  38:  26 
  • 3 Burckhardt S. Synlett  2000,  559,  and references therein
  • 4 Claremon DA. Philips BT. Tetrahedron Lett.  1988,  29:  2155 
  • 5 Miller CP. Kaufman DH. Synlett  2000,  1169-1171  
  • 6 Maugin N. Wagner A. Mioskowski C. Tetrahedron Lett.  1997,  38:  1547 
  • 7 Creedon SM. Crowley K. McCarthy DG. J. Chem Soc. Perkin Trans 1  1998,  1015 
  • 8a Rinner U. Adams DR. dos Santos ML. Abooud KA. Hudlicky T. Synlett  2003,  1247 
  • 8b Leisch H. Saxon R. Sullivan B. Hudlicky T. Synlett  2005,  445 
  • 9 Nicolaou KC. Snyder SA. Longbottom DA. Nalbandian AZ. Huang X. Chem. Eur. J.  2004,  10:  5581 
  • 10 Nicolaou KC. Longbottom DA. Snyder SA. Nalbanadian AZ. Huang X. Angew. Chem. Int. Ed.  2002,  41:  3866 
  • 11 Nicolaou KC. Snyder SA. Nalbanadian AZ. Longbottom DA. J. Am. Chem. Soc.  2004,  126:  6234 
  • 12 Wodka D. Robbins M. Lan P. Martinez RL. Athanasopoulos J. Makara GM. Tetrahedron Lett.  2006,  47:  1825 
  • 13 Banfield S. Omori AT. Leisch H. Hudlicky T. J. Org. Chem.  2007,  72:  4989 
  • 14 Raghavan S. Mustafa S. Rathore K. Tetrahedron Lett.  2008,  49:  4256