Effect of the tether length upon Truce‐Smiles rearrangement reactions
作者： David Fuss , Yu Qi Wu , Michael R. Grossi , Joshua W. Hollett , Tabitha E. Wood
DOI: 10.1002/POC.3742
关键词: Reactivity (chemistry) 、 Chemistry 、 Nucleophilic aromatic substitution 、 Nucleophile 、 Carbanion 、 Photochemistry 、 Smiles rearrangement 、 Substitution reaction 、 Nucleophilic substitution 、 Ring strain
摘要: This report examines the effect of substrate design upon Truce-Smiles rearrangement, an intramolecular nucleophilic aromatic substitution reaction. The length molecular spacer that tethers carbanion nucleophile to substituted benzene ring was found have a strong influence on ability undergo reaction successfully. Our experimental results show highest yield desired aryl migration product for substrates designed with 3-atom tether, which proceed through 5-membered spirocyclic intermediate. are interpreted in comparison survey rearrangements described literature and be consistent. Computational studies support observed reactivity trend suggest explanation favorable combination strain electrostatic repulsion leading optimal tether. Comparison our trends related ring-closing reactions illustrate unique features system studied herein.
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