ChemPlusChem p. 1078 - 1095 (2017)
Update date:2022-08-04
Topics:
Harig, Marco
Neumann, Beate
Stammler, Hans-Georg
Kuck, Dietmar
This study presents a potential experimental approach to the still elusive topologically nonplanar (K5) 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 34–36, tribenzotriquinacene 37, and tetramethoxycentrohexaindane 9. Spirane 30 and propellane 36 are characterized by X-ray structure analysis. Ozonolysis of 32 and 33 gives a keto ester (59) and a dimethyl muconate (60), respectively. Dimethoxytriptindane 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 C3 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.
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Doi:10.1016/S0040-4039(00)73893-7
(1993)Doi:10.1016/S0040-4039(00)61373-4
(1993)Doi:10.1246/bcsj.66.2987
(1993)Doi:10.1016/0223-5234(93)90042-D
(1993)Doi:10.1039/b009206l
(2001)Doi:10.3390/ijms22094318
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