An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau

Harig M, Neumann B, Stammler H-G, Kuck D (2017)
CHEMPLUSCHEM 82(7): 1078-1095.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
This study presents a potential experimental approach to the still elusive topologically nonplanar (K-5) parent hydrocarbon, centrohexaquinane (1), by a construction-dismantling (aufbau-abbau) strategy via electron-rich aromatic centropolyindanes. A series of veratrole-based centropolyindanes are synthesized and subjected to ozonolytic degradation. These include the 2,2'-spirobiindanes 30-32, fuso-diindane 33, triptindanes 3436, tribenzotriquinacene 37, and tetramethoxycentrohexaindane 9. Spirane 30 and propellane 36 are characterized by Xray structure analysis. Ozonolysis of 32 and 33 gives a keto ester (59) and a dimethyl muconate (60), respectively. Dime-thoxytriptindane 34 gives a [3.3.3] propellane-cis, cis-muconate (61) in good yield, the stereochemistry of which is determined by X-ray structure analysis. Tetramethoxytriptindane 35 gives the [3.3.3] propellane-bis-muconate 62 along with a [3.3.3] propellane-dialdehyde-muconate (63). Hexamethoxytriptindane 36 furnishes three products of mainly intra-dimethoxy cleavage, with the [3.3.3] propellane-tris-muconate 64 as the major component. X-ray structure analysis of 64 reveals molecular C-3 symmetry and all-cis, cis stereochemistry of the three muconate groups. Hexamethoxytribenzotriquinacene 37 gives the triquinacene-tris-muconate 68, albeit in very low yield. Ozonolysis of tetramethoxycentrohexaindane 9 affords the bis-muconate 10 in moderate yield, along with two further centrohexacyclic products of single-wing degradation.
Erscheinungsjahr
Zeitschriftentitel
CHEMPLUSCHEM
Band
82
Zeitschriftennummer
7
Seite
1078-1095
ISSN
PUB-ID

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Harig M, Neumann B, Stammler H-G, Kuck D. An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau. CHEMPLUSCHEM. 2017;82(7):1078-1095.
Harig, M., Neumann, B., Stammler, H. - G., & Kuck, D. (2017). An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau. CHEMPLUSCHEM, 82(7), 1078-1095. doi:10.1002/cplu.201700090
Harig, M., Neumann, B., Stammler, H. - G., and Kuck, D. (2017). An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau. CHEMPLUSCHEM 82, 1078-1095.
Harig, M., et al., 2017. An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau. CHEMPLUSCHEM, 82(7), p 1078-1095.
M. Harig, et al., “An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau”, CHEMPLUSCHEM, vol. 82, 2017, pp. 1078-1095.
Harig, M., Neumann, B., Stammler, H.-G., Kuck, D.: An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau. CHEMPLUSCHEM. 82, 1078-1095 (2017).
Harig, Marco, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. “An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau”. CHEMPLUSCHEM 82.7 (2017): 1078-1095.