2,4-Methano-2,4-dehydroadamantane. A [3.1.1]propellane

Mlinaric-Majerski, K.; Majerski, Zdenko

doi:10.1021/ja00524a033

Cited by 29 publications

(6 citation statements)

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“…9 We became interested in carbenes as intermediates during the preparation of strained polycyclic molecules, 10 particularly propellanes. 11,12 Convenient precursors for photochemical or thermal formation of carbenes are diazirine derivatives. 13 Elimination of nitrogen occurs upon photochemical excitation or at elevated temperatures, thus delivering carbenes.…”

Section: Introductionmentioning

confidence: 99%

Photoelimination of nitrogen from adamantane and pentacycloundecane (PCU) diazirines: a spectroscopic study and supramolecular control †

Šumanovac

Alešković

Šekutor

et al. 2019

Photochem Photobiol Sci

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Section: Introductionmentioning

confidence: 99%

Photoelimination of nitrogen from adamantane and pentacycloundecane (PCU) diazirines: a spectroscopic study and supramolecular control †

Šumanovac

Alešković

Šekutor

et al. 2019

Photochem Photobiol Sci

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“…[20] Z. Majerski spent his postdoctoral study (1968)(1969)(1970) with Prof. von Schleyer, where he developed his scientific interest on strained hydrocarbons. The non-standard stereochemistry of carbon atoms in such molecules had intrigued Zdenko Majerski and Kata Mlinarić-Majerski to synthesize and study reactivity of propellanes, [21,22] however later on, they continued with chemistry of adamantane. [23][24][25] The results were presented in a book chapter by K. Mlinarić-Majerski.…”

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confidence: 99%

A Strong Link Between Organic Chemistry and Chemical Crystallography Started a Century Ago

Kojić‐Prodić

Molčanov

2019

Croat. chem. acta (Online)

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The article sheds light on some historical crossings of organic chemistry and chemical crystallography. It connects past and present bringing into the focus Prof. Kata Mlinarić-Majerski’s research. An impact of structural chemistry on organic synthesis and reactivity is shown. X-ray structure analysis was established as a unique method to determine the composition and architecture of synthetic and natural organic molecules, already in the second decade of the last century; some of historical and scientific milestones are shown. Numerous controversies were solved, when intriguing molecular structures had been determined and the nature of chemical bond was clarified. An absolute structure (chirality) determination using an anomalous dispersion of X-rays was an important step forward, particularly in pharmaceutical industry. Structural data provided by X-ray crystallography, stored by Cambridge Structural Data Centre have been of great impact on many areas of science. They are closely related to intra- and intermolecular forces and structure/function correlations directing us to synthesis of compounds with designed properties. The developments of supramolecular chemistry, crystal engineering, materials science, and most of all of molecular machines have been assisted by chemical crystallography. The essay does not aim to review the complete scientific opus of Prof. K. Mlinarić-Majerski but it is focused on some of the highlights of her research. The interdisciplinary approach in her research is related to the use of X-ray structural analysis to define molecular architecture, conformational chirality, conformational isomerism, and get insight into reaction paths, interactions governing molecular assembling, and to recognise chemical properties of new compounds. In these researches the X-ray crystallographers were involved.

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“…[4.1.1] 螺桨烷, 20,21 [3.1.1] 螺桨烷及其衍生物, 22,23 [3.2.l]螺桨烷 24,25 等一系列化合物. 除了全碳型的螺桨烷外, 含重原子的螺桨烷 E5R6 (E=Si, Ge, Sn)及其衍生物在实验和理论上也引起了广泛的关注.…”

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Structures and Properties of BX[(CH2)n]3 and BX(CH2)[CH(CH2)nCH] (X=N, P) with the [n.n.n]propellane Configuration

Li¹,

Zhang²

2014

Acta Physico-Chimica Sinica

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的结构、稳定性、化学键和电子光谱性质. 计算结果表明这些分子都是稳定的. BX[(CH2)n]3 (X=N, P; n=1-6)的最高占据分子轨道(HOMO)和最低空分子轨道(LUMO)之间的能隙均大于 5.20 eV, 其中 BN[CH2]3和 BP[CH2]3 的能隙超过 7.0 eV, 与 C5H6的能隙(7.27 eV)很接近, BX(CH2)[CH(CH2)nCH] (X=N, P; n=1-6)的能隙在 6.80 eV 左右. 所研究分子能量的二阶差分表明 BN[(CH2)3]3、 BP[(CH2)4]3 及 BX(CH2)[CH(CH2)2CH] (X=N, P)是最稳定的. BX[(CH2)n]3的 Wiberg 键级表明除了 BN[(CH2)n]3 (n=2 和 6)中不存在 B-N 键, 其它化合物中 B 和 N 均形成了化学键, BP[(CH2)n]3中除了 BP[(CH2)2]3不存在 B-P 键, 其它的均存在. 电子密度的拓扑分析表明 N-B 键属于离子键, 而 P-B 键具有共价键特征. BX[(CH2)n]3 (X=N, P)的第一垂直激发能分别在 191.1-284.8 nm 和 191.8-270.1 nm 之间, BX(CH2)[CH(CH2)nCH] (X=N, P)的第一垂直激发能分别在 190.5-199.7 nm 和 209.0-221.3 nm 之间. 关键词: [n.n.n]螺桨烷; BX[(CH2)n]3; BX(CH2)[CH(CH2)nCH]; 稳定性; 化学键; 电子光谱中图分类号: O641 Structures and Properties of BX[(CH 2) n ] 3 and BX(CH 2)[CH(CH 2) n CH] (X=N, P) with the [n.n.n]propellane Configuration

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2,4-Methano-2,4-dehydroadamantane. A [3.1.1]propellane

Abstract: 2) The synthesis proceeds through the key intermediate, 2-deuterio-2-phenylethanol, a compound whose synthesis and chiroptical properties have been completely documented by R. L. Elsenbaumer and H. S.

Cited by 29 publications

References 1 publication

Photoelimination of nitrogen from adamantane and pentacycloundecane (PCU) diazirines: a spectroscopic study and supramolecular control †

Photoelimination of nitrogen from adamantane and pentacycloundecane (PCU) diazirines: a spectroscopic study and supramolecular control †

A Strong Link Between Organic Chemistry and Chemical Crystallography Started a Century Ago

Structures and Properties of BX[(CH<sub>2</sub>)<sub><em>n</em></sub>]<sub>3</sub> and BX(CH<sub>2</sub>)[CH(CH<sub>2</sub>)<sub><em>n</em></sub>CH] (X=N, P) with the [<em>n.n.n</em>]propellane Configuration

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