Scholl-Type Cycloheptatriene Ring Closure of 1,4,9,12-Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane-Based Polyaromatic Saddles.

Wong W-S, Lau W-W, Li Y, Liu Z, Kuck D, Chow H-F (2019)
Chemistry : chem.201904949.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Autor*in
Wong, Wai-Shing; Lau, Wing-Wa; Li, Yuke; Liu, Zhifeng; Kuck, DietmarUniBi; Chow, Hak-Fun
Abstract / Bemerkung
The Scholl-type cyclodehydrogenation generating up to four cycloheptatriene rings around a fenestrindane core leads to novel, saddle-shaped polyaromatic hydrocarbon derivatives. In this article, we present the results of in-depth experimental and computational works on the oxidative cyclization of various 1,4,9,12-tetraarylfenestrindanes. In particular, the kinetic control of the four-step cyclization of the electronically activated tetrakis(3,4-dimethoxyphenyl) derivative is elucidated. The reasons for the exclusive emergence of one single among the three possible doubly cyclized intermediates and for the nonappearance of the singly and triply cyclized intermediates are clarified. In addition, the origin of the concomitant bridgehead hydroxylation is studied. The reactivity of a set of fifteen symmetrically and unsymmetrically substituted 1,4,9,12-tetraarylfenestrindanes towards Scholl-type cyclodehydrogenation is presented, pinpointing the structural factors that underlie this reaction and demonstrating the potential and limitations of this synthetic approach. A particularly surprising finding of this study is that the electronically nonactivated 1,4,9,12-tetraphenylfenestrindane can also undergo the fourfold Scholl-type cyclization process and can be transformed to the parent saddle hydrocarbon. © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Erscheinungsjahr
2019
Zeitschriftentitel
Chemistry
Art.-Nr.
chem.201904949
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2939580

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Wong W-S, Lau W-W, Li Y, Liu Z, Kuck D, Chow H-F. Scholl-Type Cycloheptatriene Ring Closure of 1,4,9,12-Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane-Based Polyaromatic Saddles. Chemistry . 2019: chem.201904949.
Wong, W. - S., Lau, W. - W., Li, Y., Liu, Z., Kuck, D., & Chow, H. - F. (2019). Scholl-Type Cycloheptatriene Ring Closure of 1,4,9,12-Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane-Based Polyaromatic Saddles. Chemistry , chem.201904949. doi:10.1002/chem.201904949
Wong, W. - S., Lau, W. - W., Li, Y., Liu, Z., Kuck, D., and Chow, H. - F. (2019). Scholl-Type Cycloheptatriene Ring Closure of 1,4,9,12-Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane-Based Polyaromatic Saddles. Chemistry :chem.201904949.
Wong, W.-S., et al., 2019. Scholl-Type Cycloheptatriene Ring Closure of 1,4,9,12-Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane-Based Polyaromatic Saddles. Chemistry , : chem.201904949.
W.-S. Wong, et al., “Scholl-Type Cycloheptatriene Ring Closure of 1,4,9,12-Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane-Based Polyaromatic Saddles.”, Chemistry , 2019, : chem.201904949.
Wong, W.-S., Lau, W.-W., Li, Y., Liu, Z., Kuck, D., Chow, H.-F.: Scholl-Type Cycloheptatriene Ring Closure of 1,4,9,12-Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane-Based Polyaromatic Saddles. Chemistry . : chem.201904949 (2019).
Wong, Wai-Shing, Lau, Wing-Wa, Li, Yuke, Liu, Zhifeng, Kuck, Dietmar, and Chow, Hak-Fun. “Scholl-Type Cycloheptatriene Ring Closure of 1,4,9,12-Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane-Based Polyaromatic Saddles.”. Chemistry (2019): chem.201904949.

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