Rearrangements of Cycloalkenyl Aryl Ethers.
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.
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary. torincsi@mail.bme.hu.
Mercedesz
M
Törincsi
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary. nagymelynda@freemail.hu.
Melinda
M
Nagy
Research Centre for Natural Sciences of the Hungarian Academy of Sciences, Department of Theoretical Chemistry, Magyar Tudósok Körútja 2, Budapest 1117, Hungary. bihari.tamas@ttk.mta.hu.
Tamás
T
Bihari
Research Centre for Natural Sciences of the Hungarian Academy of Sciences, Department of Theoretical Chemistry, Magyar Tudósok Körútja 2, Budapest 1117, Hungary. stirling.andras@ttk.mta.hu.
András
A
Stirling
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary. Kolonits@mail.bme.hu.
Pál
P
Kolonits
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary. lnovak@mail.bme.hu.
Lajos
L
Novak
D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
D004987:Ethers; D009281:Naphthalenes; D010636:Phenols
Claisen rearrangement; Cope rearrangement; naphthyl ethers; phenol ethers; reaction mechanism