Benzoanellated centropolyquinanes, 12. Trifuso-centrotetraindan - two syntheses of a new centropolyindan

Kuck D, Seifert M (1992)
Chemische Berichte 125(6): 1461-1469.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Kuck, DietmarUniBi; Seifert, Monika
Abstract / Bemerkung
Two independent syntheses of the new centrotetraindan 2, a trifuso, Cs-symmetrical isomer of fenestrindan 1, are described. The first approach is based on the endo-phenyldiindanone 7, which is converted into 2 by benzylation to ketone 8 and subsequent cyclodehydration with polyphoshoric acid. The second, more efficient approach is based on the diindan-dione 17, which is converted into ketol 19 in two steps, which, in turn, is subjected to a three-step cyclodehydration-reduction-cyclodehydration sequence via 26 and 27 to give 2 in 8% overall yield. Some limits of the cyclodehydration of diindan alcohols and ketones are demonstrated with regard to effects of steric crowding and fragmentation of the carbon skeleton. The steric hindrance of endo-phenyl-substituted diindans is demonstrated in the case of ketone 26.
Stichworte
Cyclodehydration; Centropolyindans; Polycyclic compounds; Propellanes; Triquinacenes
Erscheinungsjahr
1992
Zeitschriftentitel
Chemische Berichte
Band
125
Ausgabe
6
Seite(n)
1461-1469
ISSN
0009-2940
eISSN
1099-0682
Page URI
https://pub.uni-bielefeld.de/record/1774242

Zitieren

Kuck D, Seifert M. Benzoanellated centropolyquinanes, 12. Trifuso-centrotetraindan - two syntheses of a new centropolyindan. Chemische Berichte. 1992;125(6):1461-1469.
Kuck, D., & Seifert, M. (1992). Benzoanellated centropolyquinanes, 12. Trifuso-centrotetraindan - two syntheses of a new centropolyindan. Chemische Berichte, 125(6), 1461-1469. doi:10.1002/cber.19921250624
Kuck, D., and Seifert, M. (1992). Benzoanellated centropolyquinanes, 12. Trifuso-centrotetraindan - two syntheses of a new centropolyindan. Chemische Berichte 125, 1461-1469.
Kuck, D., & Seifert, M., 1992. Benzoanellated centropolyquinanes, 12. Trifuso-centrotetraindan - two syntheses of a new centropolyindan. Chemische Berichte, 125(6), p 1461-1469.
D. Kuck and M. Seifert, “Benzoanellated centropolyquinanes, 12. Trifuso-centrotetraindan - two syntheses of a new centropolyindan”, Chemische Berichte, vol. 125, 1992, pp. 1461-1469.
Kuck, D., Seifert, M.: Benzoanellated centropolyquinanes, 12. Trifuso-centrotetraindan - two syntheses of a new centropolyindan. Chemische Berichte. 125, 1461-1469 (1992).
Kuck, Dietmar, and Seifert, Monika. “Benzoanellated centropolyquinanes, 12. Trifuso-centrotetraindan - two syntheses of a new centropolyindan”. Chemische Berichte 125.6 (1992): 1461-1469.
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