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2005
Oxidation
O 0212
32- 057
Reactions of 1-Naphthols with π-Acceptor p-Benzoquinones: Oxidative Aryl
Coupling vs. Non-Oxidative Electrophilic Arylation. — The reactions of various
1-naphthols with different p-benzoquinones as π-electron acceptors are studied. The reactions depend on the electron-donating or -accepting ability of the naphthols, reflected
in the first oxidation or reduction potential of these compounds. Thus, oxidative biaryl
coupling and subsequent dehydrogenation to (II) or (IV) take place with electron-rich
naphthols such as (I) or (III). In the case of the electron-deficient naphthol (VII), two
different types of reactions occur in the presence of ZrO2 or SnCl 4: ZrO2 promotes the
electrophilic arylation to (IX), while SnCl4 mediates the oxidative trimerization to (X).
The different reaction mechanism are discussed. — (TAKEYA*, T.; KONDO, H.;
OTSUKA, T.; DOI, H.; OKAMOTO, I.; KOTANI, E.; Chem. Pharm. Bull. 53 (2005)
2, 199-206; Showa Pharm. Univ., Machida, Tokyo 194, Japan; Eng.) — H. Haber
2005
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