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Molecules 2016, 21(4), 503; doi:10.3390/molecules21040503

Rearrangements of Cycloalkenyl Aryl Ethers

1
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4, Budapest 1111, Hungary
2
Research Centre for Natural Sciences of the Hungarian Academy of Sciences, Department of Theoretical Chemistry, Magyar Tudósok Körútja 2, Budapest 1117, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Mark A. Rizzacasa
Received: 14 January 2016 / Revised: 7 April 2016 / Accepted: 12 April 2016 / Published: 19 April 2016
(This article belongs to the Special Issue Pericyclic Reactions)
View Full-Text   |   Download PDF [2175 KB, uploaded 19 April 2016]   |  

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. View Full-Text
Keywords: Claisen rearrangement; Cope rearrangement; phenol ethers; naphthyl ethers; reaction mechanism Claisen rearrangement; Cope rearrangement; phenol ethers; naphthyl ethers; reaction mechanism
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MDPI and ACS Style

Törincsi, M.; Nagy, M.; Bihari, T.; Stirling, A.; Kolonits, P.; Novak, L. Rearrangements of Cycloalkenyl Aryl Ethers. Molecules 2016, 21, 503.

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