Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution

Kuck D, Schuster A, Gestmann D, Posteher F, Pritzkow H (1996)
CHEMISTRY-A EUROPEAN JOURNAL 2(1): 58-67.

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Abstract
Syntheses, properties, and some reactions of a novel centropolycyclic hydrocarbon, centropentaindan (1), are described. The molecular structure of 1 consists of a tetrabenzo[5.5.5.5]fenestrane bearing a fifth centrically fused indan unit. Independent syntheses have been developed employing i) twofold cyclodehydrogenation of tribenzotriquinacene (7) with Pd/C at 500 degrees C, which gives 1 in 50 % yield, and ii) a two-step procedure by te-trabromination of di-fuso-centrotriindan (8) followed by condensation with two molecules of benzene, which provides 1 in 88% yield. Some bridgehead-substituted centropentaindans are described, including the highly labile dibromo derivative 19, and the centrohexacyclic, topologically nonplanar endo-peroxide 26 and endo-disulfide 28. The notably rigid ring fusion in the molecular framework of 1 is shown both by X-ray structural analysis and by particular steric interactions of the two mutually compressed bridgehead substituents.
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Kuck D, Schuster A, Gestmann D, Posteher F, Pritzkow H. Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution. CHEMISTRY-A EUROPEAN JOURNAL. 1996;2(1):58-67.
Kuck, D., Schuster, A., Gestmann, D., Posteher, F., & Pritzkow, H. (1996). Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution. CHEMISTRY-A EUROPEAN JOURNAL, 2(1), 58-67.
Kuck, D., Schuster, A., Gestmann, D., Posteher, F., and Pritzkow, H. (1996). Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution. CHEMISTRY-A EUROPEAN JOURNAL 2, 58-67.
Kuck, D., et al., 1996. Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution. CHEMISTRY-A EUROPEAN JOURNAL, 2(1), p 58-67.
D. Kuck, et al., “Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 2, 1996, pp. 58-67.
Kuck, D., Schuster, A., Gestmann, D., Posteher, F., Pritzkow, H.: Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution. CHEMISTRY-A EUROPEAN JOURNAL. 2, 58-67 (1996).
Kuck, Dietmar, Schuster, A, Gestmann, D, Posteher, F, and Pritzkow, H. “Centropentaindan, a fenestrane bearing five mutually fused indan units: Syntheses, molecular structure, and bridgehead substitution”. CHEMISTRY-A EUROPEAN JOURNAL 2.1 (1996): 58-67.
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