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

Abstract

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.