Self-condensation of 1-bromo-2-naphthol: mechanism of formation of a 1,4-dinaphthodioxin
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 6,p. 1291-1293
- https://doi.org/10.1039/p29940001291
Abstract
The reaction of 1-bromo-2-naphthol with its conjugated base (sodium 1-bromo-2-naphthoxide) affords 1-bromo-2′-hydroxy-2,1′-dinaphthyl ether and follows a second-order kinetic law. The bromo ether can be cyclised to a 1,4-dioxin derivative through a radical ipso-substitution reaction, predominantly. Some mechanistic implications are discussed.Keywords
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