Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 1, Pages 105-110Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301460
Keywords
Atropisomerism; Host-guest systems; Supramolecular chemistry; Biaryls; Conformation analysis
Categories
Funding
- American Chemical Society Petroleum Research Fund (PRF) [51053-ND4]
- Department of Chemistry and Biochemistry at Ohio University
- College of Arts and Sciences at Ohio University
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The torsional barrier of biphenyls bearing a prochiral dimethylsulfonium group at their 3-position could be determined by variable-temperature H-1 NMR spectroscopy only after encapsulation into cucurbit[7]- or -[8]uril, which triggered the splitting of the two methyl signals. Confinement of the biphenyl units into the macrocycles amplifies the dissymmetry caused by the various ortho- and ortho-substituents and represents a new tool that can be used to access atropisomerization barriers of bi(hetero)aryl derivatives.
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