1502. Burgess Reagent

Nomenclature

CAS number: 29684-56-8
N,N-Diethyl-N-[[(methoxycarbonyl)amino]sulfonyl]ethanaminium inner salt; (methoxycarbonylsulfamoyl)triethylammonium hydroxide inner salt; methyl(carboxysulfamoyl)triethylammonium hydroxide inner salt; methyl-N-(triethylammoniumsulfonyl)carbamate.
C8H18N2O4S; mol wt 238.30.
C 40.32%, H 7.61%, N 11.76%, O 26.86%, S 13.46%.

Description and references

Dehydrating agent. Synthesis method: G. M. Atkins, Jr., E. M. Burgess, J. Am. Chem. Soc. 90, 4744 (1968). Prepn and applications in dehydration reactions: E. M. Burgess et al., ibid. 92, 5224 (1970); eidem, J. Org. Chem. 38, 26 (1973). Prepn and reaction with primary alcohols to form urethanes: E. M. Burgess et al., Org. Synth. 56, 40 (1977). Reaction with epoxides: U. Rinner et al., Synlett 2003, 1247. Review of chemistry: C. Lamberth, J. Prakt. Chem. Chem.-Ztg. 342, 518-522 (2000); K. C. Nicolaou et al., Chem. Eur. J. 10, 5581-5606 (2004).

Chemical structure

Properties

Colorless needles from toluene, mp 71-72°.

Use

Reagent for dehydration of secondary and tertiary alcohols; source of heteroatoms (N, O, S) in organic synthesis.