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

Giles, R.G.F., Green, I.R., Niven, M.L., Yorke, S.C. and Hugo, V.I. (1986) Trifluoroacetylation of Oxygenated Naphthalenes. Synthesis of some Naphtho[2,3 c]pyran 5,10 quinones. South African Journal of Chemistry, 39 (1). pp. 46-50.

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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.

Publication Type: Journal Article
Publisher: South African Bureau for Scientific Publications
Copyright: © 1986 South African Chemical Institute (SACI)
URI: http://researchrepository.murdoch.edu.au/id/eprint/35678
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