Burgess reagent
Chemical compound
From Wikipedia, the free encyclopedia
The Burgess reagent (methyl N-(triethylammoniumsulfonyl)carbamate) is a mild and selective zwitterionic dehydrating reagent used in organic chemistry.[1][2] It was developed in the laboratory of Edward M. Burgess at Georgia Tech.
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| Names | |
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| IUPAC name
1-Methoxy-N-triethylammoniosulfonyl-methanimidate | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.157.812 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H18N2O4S | |
| Molar mass | 238.30 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| 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. A general mechanism is shown below:
Preparation
The reagent is prepared from chlorosulfonylisocyanate by stepwise reaction with methanol and triethylamine in warm benzene, all reagents and solvents must be kept anhydrous:[3]
