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31.21.1.97.3 Variation 3: Using Trifluoroperoxyacetic Acid

DOI: 10.1055/sos-SD-031-01277

Aitken, K. M.; Aitken, R. A.Science of Synthesis, (2007311297.

The fluorinated derivative of peracetic acid is a widely used oxidant of aromatic amines to nitroarenes. It is strong enough to oxidize electron-poor amines but compatible with a variety of functional groups. The reagent is typically prepared from trifluoroacetic acid or anhydride and hydrogen peroxide in the cold before addition of the amine to the reaction mixture, e.g. in the synthesis of 186 (Scheme 147).[‌445‌] A selection of transformations performed this way is presented in Table 25.[‌446‌‌457‌]

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8-(8-eeeeeeeeeee)-8-eeeeee-8-eeeeeeeeeeee-8-eee MMMM, 88% M8M8, MM8Me8 eeeeee, 8e 8-eeeeee-8-(8-eeeeeeeeeee)-8-eeeeeeeeeeee-8-eee 88 [‌888‌]
8-eeeee-8-eeeee-8-eeeeeeeeeeeee eeee MMMM, 88% M8M8, MM8Me8 8°M, 8e, eeee eeee ee ee 8-eeeee-8-eeeeee-8-eeeeeeeeeeee eeee 88 [‌888‌]
8-eeeee-8-eeeeeeeeeeeeeee MMMM, 88% M8M8, MM8Me8 eeeeee, 8e 8-eeeeeee-8-eeeeeeeeeeeee 88 [‌888‌]
8-eeeeeeeeeee eeeeeeeeeeeeeee eeeeeee MMM, 88% M8M8 88°M, 8e 8-eeeeeeeeeee eeeeeeeeeeeeeee eeeeeee 88 [‌888‌]
8-(8-eeeee-8-eeeeeeeeeee)eeeeeeeeeeeeee MMMM, 88% M8M8 MM8Me8 eeeeee, 8e 8-(8-eeeee-8-eeeeeeeeeee)eeeeeeeeeeeeee 88 [‌888‌]
8-eeeee-8-eeeeee-8-eeeeeeeeeeee eeee MMM, MMMM, 88% M8M8 eeeeee, 8e 8-eeeeee-8,8-eeeeeeeeeeeeee eeee 88 [‌888‌]
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8-eeeee-8-eeeee-8,8,8-eeeeeeeeeeeeeeeeee MMMM, 88% M8M8, MeMM 88°M, 8e 8-eeeee-8,8,8-eeeeeeeee-8-eeeeeeeeeeeeee 88 [‌888‌]
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8,8,8-eeeeeeeee-8-eeeee-8-(eeeeeeeeeeeeeeeeeeeeeee)eeeeeee MMMM, 88% M8M8 8°M, 8e, eeee ee, eeeeeeeee 8,8,8-eeeeeeeee-8,8-eeeeeee-8-(eeeeeeeeeeeeeeeeeeeeeee)eeeeeee 888 [‌888‌]

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8,8,8-Meeeeeee-8-eeeeeeeeeeee (888):[‌888‌]

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