120022-86-8Relevant academic research and scientific papers
Centropentaindan, a Fenestrane Bearing Five Mutually Fused Indan Units: Synthesis, Molecular Structure, and Bridgehead Substitution
Kuck, Dietmar,Schuster, Andreas,Gestmann, Detlef,Posteher, Frank,Pritzkow, Hans
, p. 58 - 67 (2007/10/03)
Syntheses, properties, and some reactions of a novel centropolycyclic hydrocarbon, centropentaindan (1), are described.The molecular structure of 1 consists of a tetrabenzofenestrane bearing a fifth centrically fused indan unit.Independent syntheses have been developed employing i) twofold cyclodehydrogenation of tribenzotriquinacene (7) with Pd/C at 500 deg C, which gives 1 in 50percent yield, and ii) a two-step procedure by tetrabromination of di-fuso-centrotriindan (8) followed by condensation with two molecules of benzene, which provides 1 in 88percent 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. - Keywords: centropolyindans, cyclohydrogenation, fenestranes, polycycles, triquinacenes.
Benzoanellated Centropolyquinanes, 14 Synthesis of Tribenzotriquinacene by Stereocontrolled Cyclization of Phenyl-Substituted Cs-Diindans (4bα,9,9aα,10-Tetrahydroindenoindenes)
Kuck, Dietmar,Neumann, Ekkehard,Schuster, Andreas
, p. 151 - 164 (2007/10/02)
The synthesis of tribenzotriquinacene 4 by a stepwise cyclization strategy involving phenyl-substituted diindan intermediates is discussed in detail.Based on the determination of the anti (α) stereochemistry of the previously known phenyldiindanone 8 by s
