Internal base-directed regioselective aromatic Claisen rearrangements of imine derivatives
- UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
- Runzi Li (Creator)
- Institution
- The University of North Carolina at Greensboro (UNCG )
- Web Site: http://library.uncg.edu/
- Advisor
- Mitchell Croatt
Abstract: The aromatic Claisen rearrangement is a powerful sigmatropic reaction which unfortunately lacks regioselectivity. In this work, various tetralone-based imine derivative substrates featuring an intramolecular base were investigated to better understand the potential role of the tautomerization step in aromatic Claisen rearrangement regioselectivity. High regioselectivity (> 85%) for the more sterically hindered versus the less sterically hindered position was observed for a methyl oxime and for aliphatic imines. Despite steric hindrance, the allyl aryl ether’s meta substituent was found to have a significant electronic effect towards regioselectivity. As selectivity is one of the greatest challenges in organic synthesis, our research findings aim to tackle this challenge in the context of ortho-alkylation. Continued experiments which investigate the aromatic Claisen rearrangement regioselectivity of imine derivatives such as hydrazones are currently in progress.
Internal base-directed regioselective aromatic Claisen rearrangements of imine derivatives
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Created on 5/1/2024
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Additional Information
- Publication
- Thesis
- Language: English
- Date: 2024
- Keywords
- Allyl group, Aromatic Claisen rearrangement, Aromatic compounds, Imines, Regioselectivity, Selectivity
- Subjects
- Claisen rearrangement
- Aromatic compounds
- Imines