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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 ...
The classic example of a dehydration reaction is the Fischer esterification, which involves treating a carboxylic acid with an alcohol to give an ester RCO 2 H + R′OH ⇌ RCO 2 R′ + H 2 O Often such reactions require the presence of a dehydrating agent, i.e. a substance that reacts with water.
The dehydration of secondary and tertiary alcohols to yield an olefin through a sulfamate ester intermediate is called the Burgess dehydration reaction. [ 13 ] [ 14 ] [ 15 ] The reaction conditions used are typically very mild, giving it some advantage over other dehydration methods for sensitive substrates.
The compound is a reagent in organic synthesis. One application is for the dehydration of a secondary alcohol to give an alkene: [2] RCH(OH)CH 2 R' + Ph 2 S[OC(CF 3) 2 Ph] 2 → RCH=CHR' + Ph 2 SO + 2 HOC(CF 3) 2 Ph Mechanism of the dehydration using Martin's sulfurane.
This two step route is called the "indirect process". In the "direct process," the acid protonates the alkene, and water reacts with this incipient carbocation to give the alcohol. The direct process is more popular because it is simpler. The acid catalysts include phosphoric acid and several solid acids. [1]
Reagents are known that drive the dehydration of mixtures of alcohols and carboxylic acids. One example is the Steglich esterification , which is a method of forming esters under mild conditions. The method is popular in peptide synthesis , where the substrates are sensitive to harsh conditions like high heat.
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The term aldol condensation is also commonly used, especially in biochemistry, to refer to just the first (addition) stage of the process—the aldol reaction itself—as catalyzed by aldolases. However, the first step is formally an addition reaction rather than a condensation reaction because it does not involve the loss of a small molecule.