ChemInform Abstract: ETHANOADAMANTANE, THE MOST STABLE C12H18 ISOMER

Fǎrcaşiu, D.; Wiskott, E.; Ōsawa, Eiji; Thielecke, Wilfried; Engler, E. M.; Slutsky, Joel; Schleyer, P. Von R.; Kent, Gerald J.

doi:10.1002/chin.197438201

Cited by 3 publications

(6 citation statements)

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“…The 13 2). 20 This hydrocarbon has the correct symmetry but the reported 13 C NMR spectrum was different from that of our unknown molecule. 21 In order to evaluate how many structures are possible, we used the program MOLGEN 5.0 22 to generate all possible structures containing six CH and six CH 2 groups, with the only constraint being that no rings smaller than 5-membered ones are present.…”

Section: ■ Results and Discussionmentioning

confidence: 78%

“…It turned out that only five structures are topologically accessible with not more than one H-shift, and these are summarized in Table 2 carbons that can be accessed from 1 by just connecting CC bonds and by shifting no more than one hydrogen atom. Saturated tricyclic products with an as-indacene backbone are indeed formed in the butadiene trimerization step (18)(19)(20)(21), but no tricyclic saturated product with the cyclopenta[a]indene structure was found. This is quite remarkable because the isomerization of 1 with aluminum alkyls, albeit at temperatures above 200 °C, leads to the formation of monoolefins with both the cyclopent[a]indene and the asindacene backbone in a ratio of approximately 1:1.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

“…Nevertheless, 17 is still 13.5 kcal•mol −1 higher in energy than ethanoadamantane (10), which is the most stable C 12 H 18 isomer. 20 This means that the formation of 17 from 1 has to be a kinetically controlled process. This is also shown by the fact that even among the ten isomers with the same symmetry shown in Figure 2, 17 is the third highest in energy.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Technical Synthesis of 1,5,9-Cyclododecatriene Revisited: Surprising Byproducts from a Venerable Industrial Process

et al. 2019

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The synthesis of 1,5,9-cyclododecatriene by selective trimerization of butadiene catalyzed by TiCl4 and ethylaluminum sesquichloride has been commercially used since 1965. Although thoroughly investigated, not all details of the mechanism are completely understood. The recent development of a new process to produce cyclododecanone involving oxidation of 1,5,9-cyclododecatriene with N2O has led to the serendipitous discovery of an array of hitherto unknown byproducts, formed in the trimerization of butadiene: eleven tricyclic C12H20 and one tetracyclic C12H18 hydrocarbons, three of which had never been described before. The identification of these byproducts became possible by using a combination of chemical enrichment, high-resolution distillation, 13C-2D-INADEQUATE NMR, and comparison with ab initio calculated spectra, thus demonstrating the power of these combined techniques. The identification of these byproducts contributes to a better understanding of the mechanism of this centrally important reaction.

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Section: ■ Results and Discussionmentioning

confidence: 78%

Section: ■ Results and Discussionmentioning

confidence: 98%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Technical Synthesis of 1,5,9-Cyclododecatriene Revisited: Surprising Byproducts from a Venerable Industrial Process

et al. 2019

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“…Ethanoadamantanes in the ZH81 condensate were identified by characteristic ions (base peaks) of m/z = 162, 161, and 175 and compared to past results. 26,42,43 The studied C 0 , C 1 , and C 2 alkyl-substituted ethanodiamondoids consist of 1, 3, and 2 isomers (Figure 6a and Table 1) with a total level of 41.14 μg/ g. Similar to adamantanes, ethanoadamantanes with the same molecular weights are linearly distributed. The group of ethanoadamantanes (tetracyclic) generally distributes among the groups of adamantanes (tricyclic) and diamantanes (pentacyclic).…”

Section: Resultsmentioning

confidence: 97%

“…The group of ethanoadamantanes (tetracyclic) generally distributes among the groups of adamantanes (tricyclic) and diamantanes (pentacyclic). Ethanodiamondoids are currently the most thermally stable saturated hydrocarbons found in petroleum, 21,42 which suggests that crude oil has undergone high levels of thermal evolution. 3.2.3.…”

Section: Resultsmentioning

confidence: 99%

Discovery and Molecular Characterization of Organic Caged Compounds and Polysulfanes in Zhongba81 Crude Oil, Sichuan Basin, China

et al. 2020

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Deep carbonate strata in the Sichuan Basin in China mainly produce natural gas of high maturity. The discovery of uncommon condensate oil in the Zhongba gas field is of particular research interest. Condensate oil from the Zhongba81 well of the Lei3 Member of the Triassic Leikoupo Formation was comprehensively characterized using two-dimensional gas chromatography time-of-flight mass spectrometry. Abundant caged compounds (diamondoids, ethanodiamondoids, and thiadiamondoids), thiols, cyclic, and acyclic sulfides as well as polysulfanes were identified within it. High levels of diamondoids and ethanodiamondoids suggest that the condensate experienced high degrees of thermal cracking. Moderate levels of thiadiamondoids in the condensate and sulfur isotopes in abundant H 2 S show that the reservoir has undergone moderate thermochemical sulfate reduction alteration. A large number of low-molecular-weight sulfur compounds observed including thiols and polysulfanes have been preserved in the current low-temperature reservoir. More detailed information on the molecular composition of crude oil can facilitate stronger understanding of hydrocarbon accumulation and improve field exploration potential.

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Comprehensive Molecular Compositions and Origins of DB301 Crude Oil from Deep Strata, Tarim Basin, China

et al. 2020

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Natural gases in deep strata (>7000 m) in the Kuqa Depression of the Tarim Basin are abundant and well characterized, but oils and condensates are rare and poorly understood. We obtained a sample of petroleum liquid (condensate) from the deep hot reservoir (6930–7012 m, 131 °C) in well DB301 with the objective to better understand the origin and the thermal stability of petroleum in deep hot reservoirs. This sample was comprehensively characterized by two-dimensional gas chromatography–mass spectrometry and Fourier transform ion cyclotron resonance mass spectrometry. Abundant biaryl and diarylmethane compounds, diamondoid and ethanodiamondoid hydrocarbons, oxygen and sulfur compounds, and two novel basic nitrogen compounds were determined and quantified in the sample. The composition of DB301 condensate oil suggests that it was generated by coal source rock organofacies. High abundance of ethanodiamondoids with 1–2 cages was identified in coal-sourced oil for the first time. A kind of dicyclic monoterpene pinane (trans and cis iomers) was also identified in the sample, which is probably the first time for determining this kind of monoterpene in petroleum liquids. These ethanodiamondoids, basic nitrogen compounds, and pinanes have excellent thermal stability and therefore can be used as indicators of natural oil cracking.

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ChemInform Abstract: ETHANOADAMANTANE, THE MOST STABLE C12H18 ISOMER

Abstract: Übersicht über Darstellungsmethoden, Bildungsmechanismen und energetische Untersuchungen (Spannung, Stabilität).

Cited by 3 publications

References 1 publication

Technical Synthesis of 1,5,9-Cyclododecatriene Revisited: Surprising Byproducts from a Venerable Industrial Process

Technical Synthesis of 1,5,9-Cyclododecatriene Revisited: Surprising Byproducts from a Venerable Industrial Process

Discovery and Molecular Characterization of Organic Caged Compounds and Polysulfanes in Zhongba81 Crude Oil, Sichuan Basin, China

Comprehensive Molecular Compositions and Origins of DB301 Crude Oil from Deep Strata, Tarim Basin, China

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