Burgess reagent
 | |
| Names | |
|---|---|
| IUPAC name
1-methoxy-N-triethylammoniosulfonyl-methanimidate | |
| Identifiers | |
| 29684-56-8 | |
| ChemSpider | 2007108 |
| |
| Jmol-3D images | Image |
| PubChem | 2724994 |
| |
| Properties | |
| Molecular formula |
C8H18N2O4S |
| Molar mass | 238.30 g·mol−1 |
| Except where noted otherwise, data is 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.[1][2] 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 a so-called inner salt. A general mechanism is shown below.
Preparation
The reagent is prepared from chlorosulfonylisocyanate by reaction with subsequent treatment with methanol and triethylamine in benzene:[3]
References
- ↑ Atkins, G. M., Burgess, E. M. (1968). "The reactions of an N-sulfonylamine inner salt". J. Am. Chem. Soc. 90 (17): 4744–4745. doi:10.1021/ja01019a052.
- ↑ Sachin Khapli, Satyajit Dey and Dipakranjan Mal (2001). "Burgess reagent in organic synthesis" (PDF). J. Indian Inst. Sci. 81: 461–476.
- ↑ Edward M. Burgess, Harold R. Penton Jr., and E. A. Taylor (1973). "Thermal reactions of alkyl N-carbomethoxysulfamate esters". J. Org. Chem. 38 (1): 26–31. doi:10.1021/jo00941a006.