ISSN:
0947-6539
Keywords:
centropolyindans
;
cyclodehydrogenation
;
fenestranes
;
polycycles
;
triquinacenes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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°C, which gives 1 in 50% 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 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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19960020112
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