Burgess reagent

The Burgess reagent (methyl N-(triethylammoniumsulfonyl)carbamate) is a mild and selective dehydrating reagent often used in organic chemistry.^[1][2] It was developed in the laboratory of Edward M. Burgess at Georgia Tech.

Burgess reagent

Names
IUPAC name 1-Methoxy-N-triethylammoniosulfonyl-methanimidate
Identifiers
CAS Number	29684-56-8 Y
3D model (JSmol)	Interactive image
ChemSpider	2007108
ECHA InfoCard	100.157.812
EC Number	629-648-8
PubChem CID	2724994
UNII	H5HBH02LFX Y
CompTox Dashboard (EPA)	DTXSID90894112
InChI InChI=1/C8H18N2O4S/c1-5-10(6-2,7-3)15(12,13)9-8(11)14-4/h5-7H2,1-4H3 Key: YSHOWEKUVWPFNR-UHFFFAOYAN
SMILES O=S(=O)(N=C([O-])OC)[N+](CC)(CC)CC
Properties
Chemical formula	C8H18N2O4S
Molar mass	238.30 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The Burgess reagent is used to convert secondary and tertiary alcohols with an adjacent proton into alkenes. Dehydration of primary alcohols does not work well. The reagent is soluble in common organic solvents and alcohol dehydration takes place with syn elimination through an intramolecular elimination reaction. The Burgess reagent is a carbamate and an inner salt. A general mechanism is shown below.

Preparation

The reagent is prepared from chlorosulfonylisocyanate by reaction with methanol and triethylamine in benzene:^[3]