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The impact of a-trifluoromethanesulfonyl groups on the chemistry of various carbonyl groups is reported. Allylic a,a-dialkylated-a-trifluoromethanesulfonyl esters readily underwent decarboxylative allylation. a Trifluoromethylsulfonyl esters, ketones, and amides were all methylated in the presence of trimethylsilyldiazomethane. Esters afforded a mixture of O- and C-methylation; however, ketones and amides offered exclusively O-methylation, with varying degrees of E/Z selectivity, thus affording ambiphilic alkenes. a-Trifluoromethanesulfonyl ketones also exhibited keto-enol tautomerism.
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