Dimethyl sulfoxide-trifluoroacetic anhydride. New reagent for oxidation of alcohols to carbonyls

K Omura, AK Sharma, D Swern

Index: Omura,K. et al. Journal of Organic Chemistry, 1976 , vol. 41, # 6 p. 957 - 962

Full Text: HTML

Citation Number: 236

Abstract

Ta-Na, R= CH,; Ib-IVb; R= CF, dride reacts slowly with MezSO at room temperature to give acetoxydimethylsulfonium acetate (Ha), which on reaction with alcohols is converted to alkoxydimethylsulfonium acetates (IIIa); 2 reaction of the alkoxysulfonium salts (TIIa) with base yields carbonyl compounds and dimethyl sulfide. The intermediate salts (Ha) undergo the Pummerer rearrangement to acetoxymethyl methyl sulfide (IVa) at room temperat~ re.~ ...