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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：Veratrolo-结合中心喹啉的施工建设和臭氧溶解去除

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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.
机译：摘要本研究介绍了通过富含电子富含芳香的芳香Centropolyindanes的构建拆卸（Aufbau - Abbau）策略的仍然难以难以实现的拓扑非本体烃（K 5）亲本烃（1）的潜在实验方法。一系列基于维拉罗基Centropolyindanes合成并进行臭氧溶解的降解。这些包括2,2'-螺茚烷30-32，Fuso -dIIndane 33，斜茚烷34-36，呋喃啉丙烯37和四甲氧基苯甲烷己基丁烷9。螺旋30和螺旋烷36的特征在于X射线结构分析。臭氧溶解32和33给出了酮酯（59）和二甲基粘酰基（60）。二甲氧基硫酮茚满34给予[3.3.3]丙氨酸 - 顺式，顺式 - 脉酸酯（61），其立体化学通过X射线结构分析确定。四乙氧基硫酮35给出[3.3.3]丙氨酸 - 双 - 粘膜62以及[3.3.3]丙酸二丁醛 - 粘膜（63）。六甲氧基曲汀36筛选三种主要分三甲氧基裂解的产品，其中[3.3.3]丙酸铝酸酯64作为主要成分。 X射线结构分析64显示分子C 3对称性和全部，三种粘液基团的顺式立体化学。六甲氧基苯并二苯丙胺37给予TriquinaCene-Tris-粘膜68，尽管在非常低的产率。四甲氧基苯甲烷蛋白9的臭氧溶解于中等产率的双 - 粘琥珀酸盐10，以及单翼降解的两种进一步的甲基遗传产物。

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