Burgess reagent

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Burgess reagent
Burgess.svg
Names
IUPAC name
1-Methoxy-N-triethylammoniosulfonyl-methanimidate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.812 Edit this at Wikidata
EC Number
  • 629-648-8
UNII
  • 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
  • O=S(=O)(N=C([O-])OC)[N+](CC)(CC)CC
Properties
C8H18N2O4S
Molar mass 238.30 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
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).

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[edit]

The reagent is prepared from chlorosulfonylisocyanate by reaction with methanol and triethylamine in benzene:[3]

Burgess reagent

References[edit]

  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.