Irregular Centropolyindanes: Synthesis of 4b,9,13b,18-Tetrahydroindeno[1,2-a]indeno[2'',1''-b']indeno[1',2'-b]indene and Other Novel Centrotriindanes

Kuck D, Eckrich R, Tellenbröker J (1994)
Journal of Organic Chemistry 59(9): 2511-2515.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Kuck, DietmarUniBi; Eckrich, Ralf; Tellenbröker, Jörg
Abstract / Bemerkung
The syntheses of a novel tetraindan 6, containing two contiguous quaternary central carbon atoms, and of a number of other derivatives of the (unknown) ''irregular'' centrotriindan 5, is reported. Two-fold bridgehead benzylation of the C-2-symmetrical diindandione 7 followed by reduction leads to the dibenzyldiindandiols 11, which undergo 2-fold acid-catalyzed cyclodehydration (H3PO4/chlorobenzene) in moderate yield (22%) to 6. In contrast, use of xylene as the solvent gives rise to a Wagner-Meerwein rearrangement along with a single cyclodehydration step producing benzylidenetriindan 14 in good yield (70%). Monobenzyldiindandiols 10 incorporate a solvent molecule upon cyclodehydration in p-xylene to give triindan 12, whereas use of chlorobenzene yields complex mixtures of triindene 13 and its oligomers. These results shed some light on the relatively high strain of the tetraquinane skeleton of 6 and, in particular, on the reactivity of bridgehead [Delta(9b,10)]-diindenes, in line with previous results. An independent attempt to generate 6 from 2,2'-biindanyltetrol 16 gave the dibenzodioxatetraquinane 17 in low yield.
Stichworte
Polyquinenes; Benzoannelated centropolyquinanes; Polyspiranes; Carbon
Erscheinungsjahr
1994
Zeitschriftentitel
Journal of Organic Chemistry
Band
59
Ausgabe
9
Seite(n)
2511-2515
ISSN
0022-3263
eISSN
1520-6904
Page URI
https://pub.uni-bielefeld.de/record/1774199

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Kuck D, Eckrich R, Tellenbröker J. Irregular Centropolyindanes: Synthesis of 4b,9,13b,18-Tetrahydroindeno[1,2-a]indeno[2'',1''-b']indeno[1',2'-b]indene and Other Novel Centrotriindanes. Journal of Organic Chemistry. 1994;59(9):2511-2515.
Kuck, D., Eckrich, R., & Tellenbröker, J. (1994). Irregular Centropolyindanes: Synthesis of 4b,9,13b,18-Tetrahydroindeno[1,2-a]indeno[2'',1''-b']indeno[1',2'-b]indene and Other Novel Centrotriindanes. Journal of Organic Chemistry, 59(9), 2511-2515. https://doi.org/10.1021/jo00088a036
Kuck, D., Eckrich, R., and Tellenbröker, J. (1994). Irregular Centropolyindanes: Synthesis of 4b,9,13b,18-Tetrahydroindeno[1,2-a]indeno[2'',1''-b']indeno[1',2'-b]indene and Other Novel Centrotriindanes. Journal of Organic Chemistry 59, 2511-2515.
Kuck, D., Eckrich, R., & Tellenbröker, J., 1994. Irregular Centropolyindanes: Synthesis of 4b,9,13b,18-Tetrahydroindeno[1,2-a]indeno[2'',1''-b']indeno[1',2'-b]indene and Other Novel Centrotriindanes. Journal of Organic Chemistry, 59(9), p 2511-2515.
D. Kuck, R. Eckrich, and J. Tellenbröker, “Irregular Centropolyindanes: Synthesis of 4b,9,13b,18-Tetrahydroindeno[1,2-a]indeno[2'',1''-b']indeno[1',2'-b]indene and Other Novel Centrotriindanes”, Journal of Organic Chemistry, vol. 59, 1994, pp. 2511-2515.
Kuck, D., Eckrich, R., Tellenbröker, J.: Irregular Centropolyindanes: Synthesis of 4b,9,13b,18-Tetrahydroindeno[1,2-a]indeno[2'',1''-b']indeno[1',2'-b]indene and Other Novel Centrotriindanes. Journal of Organic Chemistry. 59, 2511-2515 (1994).
Kuck, Dietmar, Eckrich, Ralf, and Tellenbröker, Jörg. “Irregular Centropolyindanes: Synthesis of 4b,9,13b,18-Tetrahydroindeno[1,2-a]indeno[2'',1''-b']indeno[1',2'-b]indene and Other Novel Centrotriindanes”. Journal of Organic Chemistry 59.9 (1994): 2511-2515.
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