The electron density of α-carbon atom in methanesulfonic acid esters is lowered by the influence of the sulfonyloxy group. Consequently, methanesulfonic acid esters are attacked by nucleophilic reagents to proceed a substitution reaction at the α-carbon smoothly.
Methanesulfonic acid esters 1 and 2 are used as functional ethylation agents. For example, the indene derivative prepared by reaction of 1 with indenyllithium can serve as a ligand of catalyst 3, which can be useful in polymerization of styrenes, etc.1,2) In addition, 2 can be utilized for the synthesis of fluorine-containing ether compounds.3)
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