Regioselective oxidation of 3-monosubstituted juglone derivatives

Authors
Couladouros, EA Strongilos, AT
Citation
Ea. Couladouros et At. Strongilos, Regioselective oxidation of 3-monosubstituted juglone derivatives, TETRAHEDR L, 41(4), 2000, pp. 535-538
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
4
Year of publication
2000
Pages
535 - 538
Database
ISI
SICI code
0040-4039(20000122)41:4<535:ROO3JD>2.0.ZU;2-E
Abstract
Derivatives of 3-substituted juglones with either electron-withdrawing or - donating substituents are regioselectively oxidized to o- or p-naphthoquino nes using salcomine/air or [bis(trifluoroacetoxy)iodo]benzene, respectively . The structure of the oxidation products was confirmed by chemical transfo rmations. A correlation between chemical shift of the single quinoid proton and the quinone structure was established. (C) 2000 Elsevier Science Ltd. All rights reserved.