Luong, Hoa published the artcileImprovement in the One-Carbon Chain Extension of Esters with Dimethylsulfoxonium Methylide, HPLC of Formula: 5034-06-0, the publication is European Journal of Organic Chemistry (2013), 2013(20), 4238-4241, database is CAplus.
A recent report suggests that the reaction of dimethylsulfoxonium methylide with esters does not produce a chain-extended sulfur ylide as previously reported, but rather affords the corresponding carboxylate salt. We have investigated this assertion by using a combination of ab initio MO calculations, spiking studies, and isotopic labeling. The formation of carboxylate is unambiguously demonstrated to arise through hydrolysis involving adventitious water, principally derived from moisture in com. trimethylsulfoxonium chloride. Careful vacuum drying of this reagent diminishes the competing hydrolytic pathway resulting in higher yields for the chain-extension reaction than previously reported.
European Journal of Organic Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, HPLC of Formula: 5034-06-0.
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