Dearomatisation of 2-naphthol by oxidative nucleophilic substitution and oxidative electrophilic substitution

Autor:	Xavier Lusinchi, Humberto Arzeno, B. Mario Pinto, Reine-Marie Bergé-Lurion, Derek H. R. Barton
Rok vydání:	1984
Předmět:	chemistry.chemical_compound Electrophilic substitution Nitromethane chemistry Reagent Acetal Michael reaction Nucleophilic substitution Organic chemistry Medicinal chemistry Ethylene glycol Enone
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :2069-2076
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19840002069
Popis:	2-Naphthol has been dearomatised by oxidation with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in the presence of methanol, ethylene glycol, and 2,2-dimethylpropane-1,3-diol to give 1,1-alkoxy-naphthalen-2(1H)-ones in moderate yield. The reaction of 2-naphthol with 5,5′-ethylene bis(toluene-p-sulphonate)(Woodward's reagent) gives a good yield of 1,1-dithioacetal. Finally 2-naphthol is dearomatised by t-butyl perbenzoate. The smooth Michael addition of nitromethane to most of these 1,1-disubstituted naphthalen-2(1H)-ones has been demonstrated.
Databáze:	OpenAIRE
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