Burgess reagent

The Burgess reagent or Methyl N-(triethylammoniumsulphonyl)carbamate is a mild and selective dehydrating reagent often used in organic chemistry ^[1]. It is used to convert any alcohol with an adjacent proton into an alkene. The reagent is soluble in common organic solvents and alcohol dehydration takes place with syn elimination. The Burgess reagent is a carbamate and a so-called inner salt. A general mechanism is shows below.

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The reagent is prepared from chlorosulfonylisocyanate by reaction with subsequently methanol and triethylamine in ethanol.

References

• ^  Burgess reagent in organic synthesis Sachin Khapli, Satyajit Dey and Dipakranjan Mal J. Indian Inst. Sci., July-Aug. 2001, 81, 461–476 Online article
• ^  The reactions of an N-sulfonylamine inner salt, Atkins, G. M., Burgess, E. M. J. Am. Chem. Soc., 1968, 90, 4744–4745.