Dimethyl sulfoxide Trifluoroacetic anhydride

Alternatively, when 21 was treated with benzaldehyde diethyl acetal-hydrochloric acid, ethyl 3,5 4,6-di-0-benzylidene-L-gulonate (76) was formed in >90% yield. Diacetal 76 was efficiently oxidized to 77 (>90% yield) with dimethyl sulfoxide-trifluoroacetic anhydride, or by way of the nitrate of 76 and triethylamine. Hydrolysis of 77 then afforded ethyl L-xy(o-2-hexulosonate in 86% yield.383... 

Trifluoroacetic anhydride [407-25-0] p O O p F F Dimethyl sulfoxide See Dimethyl sulfoxide Trifluoroacetic anhydride Nitric acid, l,3,5-Triacetylhexahydro-l,3,5-triazine See Nitric acid 1,3,5-Triacetylhexahydrotriazine Nitric acid, 1,3,5-Triazine See Nitric acid 1,3,5-Triazine, etc. See other ACID ANHYDRIDES c4f6o3... 

Very few reports of competitive reactions of alcohols have appeared in activated dimethyl sulfoxide oxidations, but the results obtained from these limited studies are interesting. It is known that dimethyl sulfoxide-trifluoroacetic anhydride oxidation is selective for primary or secondary alcohols in the presence of benzylic or allylic alcohols, due to the latter alcohols being preferentially converted to trifiu-oroacetates. Additionally, secondary alcohols are known to be more reactive than primary alcohols in these oxidations, although the measured rate differences are not very high and selectivity cannot be guaranteed. 

Omura, K., Sharma, A. K., Swern, D. Dimethyl sulfoxide-trifluoroacetic anhydride. New reagent for oxidation of alcohols to carbonyls. J. 

Dimethyl sulfoxide-Oxalyl chloride, 167 Dimethyl sulfoxide-Trifluoroacetic anhydride, 168... 

Initially, Swem et al. reported the oxidation of sterically hindered alcohols to carbonyls with a dimethyl sulfoxide-trifluoroacetic anhydride complex.7 These reactants included primary alcohols such as 2,2-dimethyl-l-phenyl-propanol 3 and secondary alcohols, for example, 2-adamantanol 4. 

Related Reagents. A/-Chlorosuccinimide-Dimethyl Sulfide Chromic Acid Dimethyl Sulfide-Chlorine Dimethyl Sulfoxide-Acetic Anhydride Dimethyl Sulfoxide-Dicyclo-hexylcarbodiimide Dimethyl Sulfoxide-Oxalyl Chloride Dimethyl Sulfoxide-Phosphorus Pentoxide Dimethyl Sulfoxide-Sulfur Trioxide/Pyridine Dimethyl Sulfoxide-Trifluoroacetic Anhydride Dimethyl Sulfoxide-Triphosgene Manganese Dioxide Pyridinium Chlorochromate Pyridinium Dichromate Ruthenium(rV) Oxide Silver(I) Carbonate on Celite 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3( 1 H)-ons. 

Undesired electrophilic chlorination as a side-reaction in Swem oxidations i s avoided by use of TFAA in place of oxalyl chloride. See also Dimethyl Sulfoxide-Trifluoroacetic Anhydride. 

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