cheminform abstract: facile oxidation of fused 1,4-dimethoxybenzenes to 1,4-quinones using nbs:...

2001 oxidation, dehydrogenation oxidation, dehydrogenation O 0212 20 - 048 Facile Oxidation of Fused 1,4-Dimethoxybenzenes to 1,4-Quinones Using NBS: Fine-Tuned Control over Bromination and Oxidation Reactions. — Mild oxidative demethylation of fused dimethoxy and amino(methoxy)benzene derivatives (I), (XI), and (XIII) is successfully per- formed under optimized conditions using NBS in the presence of aqueous THF and a catalytic amount of H 2 SO 4 . Depending on the presence or absence of H 2 SO 4 and water, either oxidative demethylation or bromination, or both reactions occur, as is demonstrated for derivative (Ia). For 5-unsubstituted quinoline (VII) and for unfused derivative (IX), no oxidative demethylation takes place. — (KIM, DONG WOOK; CHOI, HAN YOUNG; LEE, KEE-JUNG; CHI, DAE YOON; Org. Lett. 3 (2001) 3, 445-447; Dep. Chem., Inha Univ., Inchon 402-751, S. Korea; EN) 1

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Page 1: ChemInform Abstract: Facile Oxidation of Fused 1,4-Dimethoxybenzenes to 1,4-Quinones Using NBS: Fine-Tuned Control over Bromination and Oxidation Reactions

2001 oxidation, dehydrogenation

oxidation, dehydrogenationO 0212

20 - 048Facile Oxidation of Fused 1,4-Dimethoxybenzenes to 1,4-QuinonesUsing NBS: Fine-Tuned Control over Bromination and OxidationReactions. — Mild oxidative demethylation of fused dimethoxy andamino(methoxy)benzene derivatives (I), (XI), and (XIII) is successfully per-formed under optimized conditions using NBS in the presence of aqueous THFand a catalytic amount of H2SO4. Depending on the presence or absence ofH2SO4 and water, either oxidative demethylation or bromination, or bothreactions occur, as is demonstrated for derivative (Ia). For 5-unsubstitutedquinoline (VII) and for unfused derivative (IX), no oxidative demethylation takesplace. — (KIM, DONG WOOK; CHOI, HAN YOUNG; LEE, KEE-JUNG;CHI, DAE YOON; Org. Lett. 3 (2001) 3, 445-447; Dep. Chem., Inha Univ.,Inchon 402-751, S. Korea; EN)

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