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Chiral 2-Aryl-2-methyl-2H-1-benzopyrans: Synthesis, characterization of enantiomers, and barriers to thermal racemization

✍ Scribed by Guenäelle Harié; André Samat; Robert Guglielmetti; Inge van Parys; Wim Saeyens; Denis de Keukeleire; Klaus Lorenz; Albrecht Mannschreck

Book ID
102861458
Publisher
John Wiley and Sons
Year
1997
Tongue
German
Weight
653 KB
Volume
80
Category
Article
ISSN
0018-019X

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✦ Synopsis

The ease of thermal breaking of the C(sp3)-0 bond of the 2-aryl-2-methyl-2H-l-benzopyrans 1-9 was evaluated by measuring the free energy (Act) of the racemization reaction of optically active compounds. The variation of AGZ of the thermal ring opening in terms of structural modifications is discussed. The synthesis of the studied compounds, the preparative separation of enantiomers by liquid chromatography, the determination of enantiomeric purity, the circular dichroism of enriched enantiomers, and the measurement of rate constants of enantiomerization by monitoring the decrease of the polarimetric angle of rotation at suitable temperatures are described.

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