Trifluoroacetic anhydride-2,6-Lutidine

The o-nitrobenzyl and p-nitrobenzyl ethers can b prepared and cleaved by many of the methods described for benzyl ethers. The p-nitrobenzyl ether is also prepared from an alcohol and p-nitrobenzyl alcohol (trifluoroacetic anhydride, 2,6-lutidine, CH2CI2, 67% yield). In addition, the o-nitrobenzyl ether can be cleaved by irradiation (320 nm, 10 min, quant, yield of carbohydrate " 280 nm, 95% yield of nucleotide ). The p-nitrobenzyl ether has been cleaved by electrolytic reduction (—1.1 V, DMF, R4N X, 60% yield) and by reduction with Na2S204 (pH 8-9, 80-95% yield). These ethers can also be cleaved oxidatively (DDQ or electrolysis) after reduction to the aniline derivative. ... 

Nazarov and related cyclizations Ferric chloride, 133 Organotin reagents, 211 Trifluoroacetic anhydride-2,6-Lutidine, 177... 

Methylenomycins.1 The cyclopentannelation reaction (12,310) has been modified to provide a general synthesis of methylenomycins. Thus, the adduct (2) of a-lithio-a-(methoxymethyl)allene (1) with 3-methyl-3-butene-2-one cyclizes to methylenomycin B (3) in the presence of trifluoroacetic anhydride and 2,6-lutidine. 

Tetroses and Pentoses. - A new synthesis of 2-0-benzyl-3,4-0-iso-propylidene-D-erythrose (2) from 2,3-0-isopropylidene-D-glyceraldehyde involved chain-extension by use of methyl tolyl sulfoxide, followed by benzylation of the new hydroxyl group to give 1. Quantitative transformation of the sulfoxide to a formyl group (l- 2) was achieved by exposure to lutidine-trifluoroacetic anhydride, then aq. sodium hydrogen carbonate. ... 

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