Triquinacene

Woodward, R. B.; Fukunaga, Tadamichi; Kelly, Robert C.

doi:10.1021/ja01069a046

Cited by 176 publications

(100 citation statements)

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“…Id, le). Sokolov [ 8] has perceived the possibility of the synthesis of shell topological compounds by dimerization of triquinacene [9] as a complex with metals. Sokolov believes that this reaction would directly give the topological compounds of pentagonal dodecahedrano (up to now it has not been obtained) with metal atoms remaining in the free internal space of this spherical molecule.…”

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confidence: 99%

Concepts of Trapping Topologically by Shell Molecules

Maciejewski

1982

Journal of Macromolecular Science: Part A - Chemistry

152

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Concepts of the synthesis of shell topological compounds, which consist of a guest molecule (or molecules) trapped by a host molecule with a spacial, egg shell-like structure are discussed. Generally, both constructing the shell molecule in the presence of a guest molecule and constructing the guest molecule In the presence of the shell (host) are ways to "shell" topological compounds. The preparation of shell molecules may consist of the completion of "preshell" molecules or of obtaining cascade branched oligomers and polymers. Cyclodextrins and aubstances like triquinance are considered to play a role in preshell molecules. Shell molecules may also be obtained by polyreaction of a monomer of the XRY type, which results In a cascade branched molecule of shell structure (spherical form). When the polyreaction is continued, the cascade branched molecule becomes a "cast" one. E is theoretically possible to enclose a guest molecule inside the shell during the cascade branching process if there is a good solvent (of high expansion coefficient value) iii respect to the growing branches, A spacially developed molecule of both "empty" and "cast" structure may be obtained also by the known "step by step" cascade branching process which Involves, for instance, a repeated cyanoethylation-reduction reaction.689

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confidence: 99%

Concepts of Trapping Topologically by Shell Molecules

Maciejewski

1982

Journal of Macromolecular Science: Part A - Chemistry

152

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“…Muller (3), Jacobson (2b), and Woodward (4) proposed that one fascinating polyquinane, triquinacene, could be dimerized to another: dodecahedrane (5). The exceptionally interesting CI3-tetraquinane, endo-tetracyclo[5.5.1.0.2~6.0'07'3]tride~ane-4,8,12-trione (I), was first prepared by Weiss and Edwards in 1968 (6), and its structure was definitively established by X-ray crystallography in 1973 (7).…”

Section: [Traduit Par La Redaction]mentioning

confidence: 99%

Weiss's endo- and exo-tetracyclo[5.5.1.0.^2,6 0^10,13]tridecane-4,8,12-trione: analysis of ¹H NMR couplings in a system of fused 5-membered rings

Bertz¹,

Zhang²,

Cook³

et al. 1994

Can. J. Chem.

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. Can. J. Chem. 72,1926Chem. 72, (1994.The configurational isomers of the title compounds consist of four fused five-membered rings. They contain tightly coupled 'H NMR spin systems, which provide excellent models for establishing the relationships between coupling constants and conformation. Complete chemical shift assignments and spin-spin coupling constants are reported for the title compounds by using high-field (500 MHz) 'H NMR techniques (e.g., 2D homonuclear and heteronuclear experiments, difference NOE enhancements, and computational spin simulations). In addition to the more familiar two-and three-bond couplings, the spectra of 1 and 2 also contain a number of long-range (four-and five-bond) couplings, which provide a stringent test of Barfield's theoretical treatment of four-bond couplings.

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“…[13] Therefore, triquinacene (8) has long been envisaged as the logical precursor of 3 (Figure 1). [14] Figure 1. Strain energies of unsaturated tricyclodecanes.…”

Section: Introductionmentioning

confidence: 99%

Syntheses, Structures, and Reactions of Highly Strained Dihydro- and Tetrahydroacepentalene Derivatives

et al. 1998

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A versatile approach towards the highly strained acepentalene 3 via the readily accessible dipotassium acepentalenediide (10 a) and the highly strained tetraenes 7 is reported. An unexpected [42] cycloaddition dimer 14 is formed upon protonation of the dipotassium acepentalenediide (10 a) in 93 % yield, and the monomeric 4,7-dihydroacepentalene (7 a), as the reactive intermediate, can be trapped with anthracene to form the corresponding Diels ± Alder adduct 16 in 15 % yield. In contrast, the highly strained, but sterically protected monomeric bridgehead ± bridgehead alkenes 7 c, d can be isolated upon reaction of 10 a or 10 b with bulky electrophiles, such as Me 3 -SiCl and Me 3 SnCl, respectively. The Xray crystal structure analysis of 7 d exhibits a highly pyramidalized central double bond. The bisstannane 7 d is an ideal precursor for acepentalene (3), which would be formed by removal of the two trimethylstannyl substituents. It can also be transmetallated to give the pure crystalline dilithium acepentalenediide (10 b) in 78 % yield. According to its 1 H, 7Li and 13 C NMR spectra, the bowl-shaped 12 p-dianion in 10 b is an aromatic species, and it undergoes a rapid bowl-to-bowl inversion at room temperature.

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Triquinacene

Cited by 176 publications

References 1 publication

Concepts of Trapping Topologically by Shell Molecules

Concepts of Trapping Topologically by Shell Molecules

Weiss's endo- and exo-tetracyclo[5.5.1.0.^2,6 0^10,13]tridecane-4,8,12-trione: analysis of ¹H NMR couplings in a system of fused 5-membered rings

Syntheses, Structures, and Reactions of Highly Strained Dihydro- and Tetrahydroacepentalene Derivatives

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Triquinacene

Cited by 176 publications

References 1 publication

Concepts of Trapping Topologically by Shell Molecules

Concepts of Trapping Topologically by Shell Molecules

Weiss's endo- and exo-tetracyclo[5.5.1.0.2,6 010,13]tridecane-4,8,12-trione: analysis of 1H NMR couplings in a system of fused 5-membered rings

Syntheses, Structures, and Reactions of Highly Strained Dihydro- and Tetrahydroacepentalene Derivatives

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Weiss's endo- and exo-tetracyclo[5.5.1.0.^2,6 0^10,13]tridecane-4,8,12-trione: analysis of ¹H NMR couplings in a system of fused 5-membered rings