Abstract
Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-substituted phenol and naphthol derivatives. In the case of cycloocthylphenyl ether the consecutive Claisen and Cope rearrangements were followed by an alkyl migration. The mechanism of this novel rearrangement reaction is also discussed.
Highlights
Phenol and its derivatives play an important role in organic chemistry
We have investigated the generality of the above discussed reaction
First we have focused on the rearrangement of three molecules: 2-(2-cyclohexene-1-yl)-phenol (4a), calculations
Summary
Phenol and its derivatives play an important role in organic chemistry. They are high useful building blocks in natural products and pharmaceuticals. Its derivatives have been successfully applied in the synthesis of molecules which are pharmacologically active inhibitors against many diseases, viruses, microbes, fungi, and enzymes [6,7,8,9,10]. Naphthols and their methyl ethers possess useful biologically activities. They show inhibitory activity with preferential inhibition on cyclooxygenase I and II [11,12]
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