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Trifluoroacetylation of Oxygenated Naphthalenes. Synthesis   of some Naphtho[2,3 c]pyran 5,10 quinones
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Trifluoroacetylation of Oxygenated Naphthalenes. Synthesis of some Naphtho[2,3 c]pyran 5,10 quinones

R.G.F. Giles, I.R. Green, M.L. Niven, S.C. Yorke and V.I. Hugo
South African Journal of Chemistry, Vol.39(1), pp.46-50
1986
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Abstract

Trifluoroacetic anhydride is shown to acylate 1,4,5-tri- and 1.4.5.7-tetramethoxynaphthalene, the former at C(3) or C(8), and the latter at C(8) exclusively. The same reagent also acylates 1-napththol and its 4,8-dialkoxy- and 4,6,8-triatkoxyderivatives to give ortto-trifluoroacetylnaphthols tn good yield. Cerium(IV) ammonium nitrate oxidation of the alkoxynaphthols gives the corresponding 2(1,1-dihydroxy-2- trifluoroethyl)-1 Anaphthoquinones. These quinones undergo hydroxypentylation of the quinonoid nucleus with 3- hydroxyhexanoic acid to give naphthol[2,3-c]pyran-5,10- quinones.

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