Burgess reagent

Names
IUPAC name

1-Methoxy-N-triethylammoniosulfonyl-methanimidate

Identifiers

CAS Number

* 29684-56-8 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 2007108

EC Number |

* 629-648-8

PubChem CID

* 2724994

UNII |

* H5HBH02LFX Y

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 pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H319, H335

GHS precautionary statements

| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

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.

## Preparation

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

## References

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". J. Indian Inst. Sci. 81: 461–476. Archived from the original on 2004-03-02. https://web.archive.org/web/20040302130947/http://journal.library.iisc.ernet.in/vol200104/paper6/sachin.pdf.
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.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Burgess reagent. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Burgess_reagent&oldid=812905"
*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …