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.