Dearomatisation of 2-naphthol by oxidative nucleophilic substitution and oxidative electrophilic substitution
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 2069-2076
- https://doi.org/10.1039/p19840002069
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.This publication has 1 reference indexed in Scilit:
- Chemistry of quinone derivatives. Quinone monoketals via hydrolysis of electrochemically derived quinone bisketalsThe Journal of Organic Chemistry, 1980