Σ-bishomoaromaticity

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σ-Bishomoaromaticity is an extreme case of the chemical bond and the aromaticity. It was found by the Prinzbach when they synthesized dodecahedrane via the Pagodane route [1] [2] [3]

Aromaticity concept of spatial and electr. structure of cyclic molec. systems displaying the effects of cyclic electron delocalization which provide for their enhanced thermodyn. stability and tendency to retain the struct. type in the course of chem. transfo-ns

In organic chemistry, the term aromaticity is used to describe a cyclic (ring-shaped), planar (flat) molecule with a ring of resonance bonds that exhibits more stability than other geometric or connective arrangements with the same set of atoms. Aromatic molecules are very stable, and do not break apart easily to react with other substances. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have special stability.

Horst Prinzbach was a German chemist and professor emeritus.

Pagodane chemical compound

Pagodane is an organic compound with formula C
20
H
20
whose carbon skeleton was said to resemble a pagoda, hence the name. It is a polycyclic hydrocarbon whose molecule has the D2h point symmetry group. The compound is a highly crystalline solid that melts at 243 °C, is barely soluble in most organic solvents and moderately soluble in benzene and chloroform. It sublimes at low pressure.

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George Andrew Olah Hungarian chemist

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Tetrahedrane chemical compound

Tetrahedrane is a platonic hydrocarbon with chemical formula C4H4 and a tetrahedral structure. The molecule is subject to considerable angle strain. A number of derivatives have been prepared. Tetrahedranes describe a class of molecules and ions with related structures, e.g. white phosphorus.

In organic chemistry, Hückel's rule estimates whether a planar ring molecule will have aromatic properties. The quantum mechanical basis for its formulation was first worked out by physical chemist Erich Hückel in 1931. The succinct expression as the 4n + 2 rule has been attributed to W. v. E. Doering (1951), although several authors were using this form at around the same time.

Dodecahedrane is a chemical compound (C20H20) first synthesised by Leo Paquette of Ohio State University in 1982, primarily for the "aesthetically pleasing symmetry of the dodecahedral framework". It is the simplest hydrocarbon with full icosahedral symmetry.

Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active. The compound was first synthesised by Adolf von Baeyer.

Baeyer–Villiger oxidation

The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899.

Wagner–Meerwein rearrangement organic reaction

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Prato reaction

The Prato reaction is a particular example of the well-known 1,3-dipolar cycloaddition of azomethine ylides to olefins. In fullerene chemistry this reaction refers to the functionalization of fullerenes and nanotubes. The amino acid sarcosine reacts with paraformaldehyde when heated at reflux in toluene to an ylide which reacts with a double bond in a 6,6 ring position in a fullerene via a 1,3-dipolar cycloaddition to yield a N-methylpyrrolidine derivative or pyrrolidinofullerene or pyrrolidino[[3,4:1,2]] [60]fullerene in 82% yield based on C60 conversion.

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Homoaromaticity special case of aromaticity in which conjugation is interrupted by a single sp³ hybridized carbon atom

Homoaromaticity, in organic chemistry, refers to a special case of aromaticity in which conjugation is interrupted by a single sp3 hybridized carbon atom. Although this sp3 center disrupts the continuous overlap of p-orbitals, traditionally thought to be a requirement for aromaticity, considerable thermodynamic stability and many of the spectroscopic, magnetic, and chemical properties associated with aromatic compounds are still observed for such compounds. This formal discontinuity is apparently bridged by p-orbital overlap, maintaining a contiguous cycle of π electrons that is responsible for this preserved chemical stability.

Sandwich compound chemical compound featuring a metal bound by haptic covalent bonds to two arene ligands

In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic covalent bonds to two arene ligands. The arenes have the formula CnHn, substituted derivatives (for example Cn(CH3)n) and heterocyclic derivatives (for example BCnHn+1). Because the metal is usually situated between the two rings, it is said to be "sandwiched". A special class of sandwich complexes are the metallocenes.

Fullerene chemistry

Fullerene chemistry is a field of organic chemistry devoted to the chemical properties of fullerenes. Research in this field is driven by the need to functionalize fullerenes and tune their properties. For example, fullerene is notoriously insoluble and adding a suitable group can enhance solubility. By adding a polymerizable group, a fullerene polymer can be obtained. Functionalized fullerenes are divided into two classes: exohedral fullerenes with substituents outside the cage and endohedral fullerenes with trapped molecules inside the cage.

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Cyclononatetraene chemical compound

Cyclononatetraene is an organic compound with the formula C9H10. It was first prepared in 1969 by protonation of the corresponding aromatic anion (described below). It is unstable and isomerizes with a half-life of 50 min at room temperature to 3a,7a-dihydro-1H-indene via a thermal 6π disrotatory electrocyclic ring closing. Upon exposure to ultraviolet light, it undergoes a photochemical 8π electrocyclic ring closing to give bicyclo[6.1.0]nona-2,4,6-triene.

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References

  1. G. K. S. Prakash, V. V. Krishnamurthy, R. Herges, R. Bau, H. Yuan, G. A. Olah, W.-D. Fessner, H. Prinzbach J. Am. Chem. Soc. 1986, 108, 836.
  2. G. K. S. Prakash, V. V. Krishnamurthy, R. Herges, R. Bau, H. Yuan, G. A. Olah, W.-D. Fessner, H. Prinzbach J. Am. Chem. Soc. 1988, 110, 7764.
  3. R. Herges, P. v. R. Schleyer, M. Schindler, W.-D. Fessner J. Am. Chem. Soc. 1991, 113, 3649.