Burgess reagent
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IUPAC name
1-methoxy-N-triethylammoniosulfonyl-methanimidate
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3D model (Jmol)
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| ChemSpider | |
| ECHA InfoCard | 100.157.812 |
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PubChem CID
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| Properties | |
| C8H18N2O4S | |
| Molar mass | 238.30 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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.
The reagent is prepared from chlorosulfonylisocyanate by reaction with subsequent treatment with methanol and triethylamine in benzene:
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