Burgess reagent

Burgess reagent

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Names
IUPAC name 1-methoxy-N-triethylammoniosulfonyl-methanimidate
Identifiers
CAS Number	29684-56-8
ChemSpider	2007108
Jmol 3D model	Interactive image
PubChem	2724994
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
Vapor pressure	{{{value}}}
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 or methyl N-(triethylammoniumsulfonyl)carbamate was developed in the laboratory of Edward M. Burgess at Georgia Tech. It is a mild and selective dehydrating reagent often used in organic chemistry. It is used to convert secondary and tertiary alcohol with an adjacent proton into alkenes. Primary alcohols do 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.

General Mechanism for the Burgess reagent.

Preparation

The reagent is prepared from chlorosulfonylisocyanate by reaction with subsequent treatment with methanol and triethylamine in benzene:

Burgess reagent