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. BurgessatGeorgia Tech.
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| IUPAC name
1-Methoxy-N-triethylammoniosulfonyl-methanimidate | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.157.812 
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H18N2O4S | |
| Molar mass | 238.30 g·mol−1 |
| Hazards | |
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| H315, H319, H335 | |
| 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).
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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.
The reagent is prepared from chlorosulfonylisocyanate by reaction with methanol and triethylamine in benzene:[3]
