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Biconcave and Convex-Concave Tribenzotriquinacene Dimers
Zhi-Min Li1, Ya-Wei Li1, Xiao-Ping Cao1
1State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering , Lanzhou University , Lanzhou , P.R. China.
Abstract:
A new chiral tribenzotriquinacene bearing an ortho-bromoaniline nucleus was synthesized and optically resolved. The individual enantiomers, the absolute configuration of which was confirmed by single-crystal X-ray structure analysis, were stereoselectively converted into the same pyrazine-fused syn-bis-TBTQ derivative by chirality-assisted Buchwald-Hartwig amination. The corresponding diastereomeric anti-dimer was obtained alongside the syn-dimer from the racemic sample under similar reaction conditions. X-ray structure analysis of the dimers confirmed the mutual biconcave and convex-concave configuration of their TBTQ moieties and the preservation of the orthogonal orientation of the indane wings within each of them.
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