Synthesis and structure of m-terphenyl thio-, seleno-, and telluroethers
- Zakai, Uzma I. Department of Chemistry and Biochemistry, The University of Arizona, Tucson, USA
- Błoch-Mechkour, Anna Department of Chemistry, University of Fribourg, Switzerland
- Jacobsen, Neil E. Department of Chemistry and Biochemistry, The University of Arizona, Tucson, USA
- Abrell, Leif Department of Chemistry and Biochemistry, The University of Arizona, Tucson, USA
- Lin, Guangxin Department of Chemistry and Biochemistry, The University of Arizona, Tucson, USA
- Nichol, Gary S. Department of Chemistry and Biochemistry, The University of Arizona, Tucson, USA
- Bally, Thomas Department of Chemistry, University of Fribourg, Switzerland
- Glass, Richard S. Department of Chemistry and Biochemistry, The University of Arizona, Tucson, USA
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11.11.2010
Published in:
- Journal of Organic Chemistry. - 2011, vol. 75, no. 24, p. 8363–8371
English
Several routes for the synthesis of m-terphenyl thio-, seleno-, and telluroethers were investigated. m-Terphenyl iodides react with diphenyl diselenides or ditellurides (CsOH·H₂O, DMSO, 110 °C) to give the desired compounds in 19−84% yield which significantly extends the previously reported such reactions because o-benzyne cannot be an intermediate as previously suggested. However, the most general synthetic route was that involving reaction of 2,6-diaryl Grignard reagents with sulfur, selenium, or tellurium electrophiles. The m-terphenyl thio-, seleno-, and telluroethers were characterized spectroscopically and, in one case, by single-crystal X-ray analysis. Certain of these compounds showed atropisomerism and barriers for interconversion of isomers were determined by variable-temperature NMR spectroscopy. The barriers for interconverting the syn and anti atropisomers increase on going from the analogous S to Se to Te compounds. Calculations on this isomerization revealed that the barriers are due to rotation about the aryl−aryl bond and that the barriers for rotation about the aryl−chalcogen bond are much lower.
- Faculty
- Faculté des sciences et de médecine
- Department
- Département de Chimie
- Language
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- English
- Classification
- Chemistry
- License
- License undefined
- Identifiers
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- RERO DOC 22346
- DOI 10.1021/jo101299x
- Persistent URL
- https://folia.unifr.ch/unifr/documents/301931
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