Burgess Reagent: From Oblivion to Renaissance in Organic Synthesis

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.

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