Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary
Melinda Nagy
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary
Tamás Bihari
Research Centre for Natural Sciences of the Hungarian Academy of Sciences, Department of Theoretical Chemistry, Magyar Tudósok Körútja 2, Budapest 1117, Hungary
András Stirling
Research Centre for Natural Sciences of the Hungarian Academy of Sciences, Department of Theoretical Chemistry, Magyar Tudósok Körútja 2, Budapest 1117, Hungary
Pál Kolonits
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary
Lajos Novak
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary
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.
