Synthese von 2,3,4,5,6,7‐Hexachlor‐8,8‐dicyanheptafulven

Roedig, Alfred; Försch, Manfred

doi:10.1002/cber.19781110732

Cited by 4 publications

(3 citation statements)

References 11 publications

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“…Several of the investigated heptafulvene derivatives have previously been synthesized (Scheme ), for example, the parent heptafulvene H1b and the substituted H1a , H1c , and H2c . − The reason that a wide range of different heptafulvene derivatives have been synthesized is likely the ability of substituted heptafulvenes to distort to a puckered structure so as to avoid any unfavorable antiaromatic character that they attain at planar conformations.…”

Section: Resultsmentioning

confidence: 99%

Substituent Effects on the Electron Affinities and Ionization Energies of Tria-, Penta-, and Heptafulvenes: A Computational Investigation

et al. 2010

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The extent of substituent influence on the vertical electron affinities (EAs) and ionization energies (IEs) of 43 substituted tria-, penta-, and heptafulvenes was examined computationally at the OVGF/6-311G(d)//B3LYP/6-311G(d) level of theory and compared with those of tetracyanoquinodimethane (TCNQ) and tetrathiafulvalene (TTF) as representing strong electron-acceptor and -donor compounds, respectively. The substituents X at the exocyclic positions of the fulvenes were either NH(2), H, or CN, while the substituents Y at the ring positions were H, Cl, F, CN, or NH(2). The variations of the EAs and IEs were rationalized by qualitative arguments based on frontier orbital symmetries for the different fulvene classes with either X or Y being constant. The minimum and maximum values found for the calculated EAs of the tria-, penta-, and heptafulvenes were 0.51-2.05, 0.24-3.63, and 0.53-3.14 eV, respectively, and for the IEs 5.27-9.96, 7.07-10.31, and 6.35-10.59 eV, respectively. Two of the investigated fulvenes outperform TCNQ (calcd EA = 2.63 eV) and one outperforms TTF (calcd IE = 6.25 eV) with regard to acceptor and donor abilities, respectively. We also evaluated the properties of bis(fulvene)s, i.e., compounds composed of a donor-type heptafulvene fused with an acceptor-type pentafulvene, and it was revealed that these bis(fulvene)s can be designed so that the IE and EA of the two separate fulvene segments are retained, potentially allowing for the design of compact donor-acceptor dyads.

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Section: Resultsmentioning

confidence: 99%

Substituent Effects on the Electron Affinities and Ionization Energies of Tria-, Penta-, and Heptafulvenes: A Computational Investigation

et al. 2010

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“…An alternate synthesis of 333 and its spectroscopic properties have been discussed. 346 Direct irradiation of the dicyanodiene 334a in benzene leads to regioselective formation of a single vinylcyclopropane (334b) via diphenylvinyl migration rather than dicyanovinyl. Sensitized irradiation of 334a does not lead to 334b, which suggests 334a undergoes di-7r-methane rearrangement from its singlet excited state.…”

Section: G Sulfur Compoundsmentioning

confidence: 99%

“…The reactivity of 343 is greater than that of Et2Hg and comparable to that of 345. The reaction of tertbutyl(trimethylsilyl)mercury (346) with ylidenemalononitriles gives A/-(trimethylsilyl)ketenimines (347). 363 Other alkyl derivatives of 346 (R = f-Bu) do not react.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Properties and reactions of ylidenemalononitriles

Freeman¹

1980

Chem. Rev.

310

150

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Gekreuzt‐konjugierte polychlorierte Cycloheptatrienderivate aus Octachlorcycloheptatrien und Hexachlortropon

et al. 1988

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Wir beschreiben eine neue, ergiebige Synthese von Hexachlortropon (6) und einige Kondensationsreaktionen von 6 zu neuen polychlorierten, gekreuzt konjugierten Cycloheptatrienderivaten. Umsetzungen von Octachlorcycloheptatrien (5) mit Benzol/CF3SO3Ag bzw. mit Phenylmalononitril (28) führen zu ersten stabilen [1.6.7]Chinarenen 19 und 29. Die Struktur von 19 wird mit Hilfe einer Röntgenstrukturanalyse bewiesen und ein Bildungsweg vorgeschlagen. Der Einfluß der Polychlorierung auf Stabilität und Elektronenspektren wird diskutiert.

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Synthese von 2,3,4,5,6,7‐Hexachlor‐8,8‐dicyanheptafulven

Cited by 4 publications

References 11 publications

Substituent Effects on the Electron Affinities and Ionization Energies of Tria-, Penta-, and Heptafulvenes: A Computational Investigation

Substituent Effects on the Electron Affinities and Ionization Energies of Tria-, Penta-, and Heptafulvenes: A Computational Investigation

Properties and reactions of ylidenemalononitriles

Gekreuzt‐konjugierte polychlorierte Cycloheptatrienderivate aus Octachlorcycloheptatrien und Hexachlortropon

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