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首页> 外文期刊>ChemPlusChem >An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau Aufbau of Veratrolo‐Annelated Centropolyquinanes and Ozonolytic Abbau Abbau
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An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau Aufbau of Veratrolo‐Annelated Centropolyquinanes and Ozonolytic Abbau Abbau

机译：难以实现Centropolyindanes背后的非芳族目标：施工建设验证结合的中心奎纳斯和臭氧溶解去除

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Abstract 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 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 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.
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