Benzoanellated centropolyquinanes, 11. Synthesis of tribenzotriquinacene and some centro-substituted derivatives

Kuck D, Lindenthal T, Schuster A (1992)
Chemische Berichte 125(6): 1449-1460.

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The syntheses of tribenzotriquinacene (1a) and five centro-substituted derivatives, 1b-1e and 1g, as well as of the related diindan 13 are reported. The three-step synthetic sequences include the reduction of suitably substituted 2-benz-hydryl-1,3-indandiones 3 to the corresponding 1,3-indandiols 4 and the twofold cyclodehydration of the latter to close two additional five-membered rings at a time. Although the yields of the cyclodehydration step 4 · 1 are only low to moderate (10-33%), the overall approach allows the preparation of 5-50-gram amounts of the centropolyindans in most cases by starting from simple 1,3-indandiones 2a-2c. This includes the new synthesis of the parent tribenzotriquinacene (1a). The related Cs-symmetrical diindan, 4b,9,9a,10-tetrahydroindeno[1,2-a]indene (13), has been prepared in high yield by using the same cyclodehydration technique. Scope and limitations of the double cyclodehydration strategy are described concerning the synthesis of 1,3-indandiones with bulky substituents at C-2 and the cyclization of 1,3-indandiols with an aptitude to undergo heterolytic cleavage of an exocyclic C-2-C- bond, in particular 4f. The course of the reduction of the 2,2-disubstituted 1,3-indandiones with lithium aluminum hydride is discussed on the basis of the stereochemistry of the product 1,3-indandiols.
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Kuck D, Lindenthal T, Schuster A. Benzoanellated centropolyquinanes, 11. Synthesis of tribenzotriquinacene and some centro-substituted derivatives. Chemische Berichte. 1992;125(6):1449-1460.
Kuck, D., Lindenthal, T., & Schuster, A. (1992). Benzoanellated centropolyquinanes, 11. Synthesis of tribenzotriquinacene and some centro-substituted derivatives. Chemische Berichte, 125(6), 1449-1460.
Kuck, D., Lindenthal, T., and Schuster, A. (1992). Benzoanellated centropolyquinanes, 11. Synthesis of tribenzotriquinacene and some centro-substituted derivatives. Chemische Berichte 125, 1449-1460.
Kuck, D., Lindenthal, T., & Schuster, A., 1992. Benzoanellated centropolyquinanes, 11. Synthesis of tribenzotriquinacene and some centro-substituted derivatives. Chemische Berichte, 125(6), p 1449-1460.
D. Kuck, T. Lindenthal, and A. Schuster, “Benzoanellated centropolyquinanes, 11. Synthesis of tribenzotriquinacene and some centro-substituted derivatives”, Chemische Berichte, vol. 125, 1992, pp. 1449-1460.
Kuck, D., Lindenthal, T., Schuster, A.: Benzoanellated centropolyquinanes, 11. Synthesis of tribenzotriquinacene and some centro-substituted derivatives. Chemische Berichte. 125, 1449-1460 (1992).
Kuck, Dietmar, Lindenthal, Thomas, and Schuster, Andreas. “Benzoanellated centropolyquinanes, 11. Synthesis of tribenzotriquinacene and some centro-substituted derivatives”. Chemische Berichte 125.6 (1992): 1449-1460.
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