Burgess reagent

Burgess reagent
Names
	IUPAC name 1-Methoxy-N-triethylammoniosulfonyl-methanimidate
Identifiers
CAS Number	29684-56-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	2007108;
ECHA InfoCard	100.157.812
EC Number	629-648-8;
PubChem CID	2724994;
UNII	H5HBH02LFX ;
CompTox Dashboard (EPA)	DTXSID90894112 ;
	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
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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. Burgess at Georgia Tech.

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.

General Mechanism for the Burgess reagent.

Preparation

The reagent is prepared from chlorosulfonylisocyanate by reaction 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 & Dipakranjan Mal (2001). "Burgess reagent in organic synthesis" (PDF). J. Indian Inst. Sci. 81: 461–476. Archived from the original (PDF) on 2004-03-02.
Edward M. Burgess; Harold R. Penton Jr. & E. A. Taylor (1973). "Thermal reactions of alkyl N-carbomethoxysulfamate esters". J. Org. Chem. 38 (1): 26–31. doi:10.1021/jo00941a006.

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[1] 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.

[2] Sachin Khapli, Satyajit Dey & Dipakranjan Mal (2001). "Burgess reagent in organic synthesis" (PDF). J. Indian Inst. Sci. 81: 461–476. Archived from the original (PDF) on 2004-03-02.

[3] Edward M. Burgess; Harold R. Penton Jr. & E. A. Taylor (1973). "Thermal reactions of alkyl N-carbomethoxysulfamate esters". J. Org. Chem. 38 (1): 26–31. doi:10.1021/jo00941a006.