Burgess Dehydrating Reagent

Burgess dehydrating reagent is efficient at generating olefins from secondary and tertiary alcohols where the first-order thermolytic Ei (during the elimination, the two groups leave at about the same time and bond to each other concurrently) mechanism prevails.

Different from the classic dehydration reaction (heating under acid or base catalysis), the substrate can be dehydrated at low temperature and neutral and mild conditions. However, it cannot be used for the dehydration reaction of primary alcohol.

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References :

[1]Burgess E M, Penton Jr H R, Taylor E A. Thermal reactions of alkyl N-carbomethoxysulfamate esters[J]. The Journal of organic chemistry, 1973, 38(1): 26-31.

[2]Stalder H. Metaboliten der 1, 5‐Dihydroimidazo [2, 1‐b] chinazolin‐2 (3H)‐one. Synthese und Reaktionen einiger 1, 5‐Dihydro‐3‐hydroxyimidazo [2, 1‐b] chinazolin‐2 (3H)‐one[J]. Helvetica chimica acta, 1986, 69(8): 1887-1897.

[3]Miller C P, Kaufman D H. Mild and efficient dehydration of oximes to nitriles mediated by the Burgess reagent[J]. Synlett, 2000, 2000(08): 1169-1171.

[4]Li J J, Li J J, Li J, et al. A synthesis of N-bridged 5, 6-bicylic pyridines via a mild cyclodehydration using the burgess reagent and discovery of a novel carbamylsulfonylation reaction[J]. Organic Letters, 2008, 10(13): 2897-2900.

[5]Nicolaou K C, Snyder S A, Longbottom D A, et al. New uses for the Burgess reagent in chemical synthesis: Methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides[J]. Chemistry–A European Journal, 2004, 10(22): 5581-5606.

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