Phosphorus pentoxide is used as a reagent in a variation of this reaction named for Albright which can be performed at room temperature. The use of TFAA allows this reaction to occur at higher temperatures but results in side products when the desired groups are not sterically hindered. A failed nucleoside coupling procedure led to the discovery of this reaction’s predecessor by Pfitzner and Moffatt, which activates the central species using DCC. In this reaction’s mechanism, a sulfur ylide decomposes after forming a five-membered ring transition state resulting in the desired product and an extremely foul smelling byproduct. The species which carries out this reaction can be produced by reacting dimethyl sulfide and chlorine in a procedure named for Corey and Kim. This reaction can be performed on compounds that might be hydrolyzed by the acidic conditions of the Jones reagent. For 10 points, name this reaction which uses oxalyl chloride to activate DMSO and converts an alcohol to a carbonyl.
Phosphorus pentoxide is used as a reagent in a variation of this reaction named for Albright which can be performed at room temperature. The use of TFAA allows this reaction to occur at higher temperatures but results in side products when the desired groups are not sterically hindered. A failed nucleoside coupling procedure led to the discovery of this reaction’s predecessor by Pfitzner and Moffatt, which activates the central species using DCC. In this reaction’s mechanism, a sulfur ylide decomposes after forming a five-membered ring transition state resulting in the desired product and an extremely foul smelling byproduct. The species which carries out this reaction can be produced by reacting dimethyl sulfide and chlorine in a procedure named for Corey and Kim. This reaction can be performed on compounds that might be hydrolyzed by the acidic conditions of the Jones reagent. For 10 points, name this reaction which uses oxalyl chloride to activate DMSO and converts an alcohol to a carbonyl.
Phosphorus pentoxide is used as a reagent in a variation of this reaction named for Albright which can be performed at room temperature.