Cyclophane series. Part 24. [2.2](1,4)Phenanthrenoparacyclophane: synthesis and two-dimensional proton and carbon-13 NMR study

Hopf, Henning; Mlynek, Cornelia; Eltamany, S. H.; Ernst, Ludger

doi:10.1021/ja00309a033

Cited by 34 publications

(16 citation statements)

References 2 publications

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“…The 'H NM R spectra of the CT complexes be tween the donors [4,5] and TCNE were measured in deuterated chloroform and the chemical shift of the aromatic protons for the free donors and their com plexes are given in Table II. The data in this Table reveal a downfield chemical shift of the arom atic pro tons in the CT complexes.…”

Section: Resultsmentioning

confidence: 99%

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Molecular Complexes of Cyclophanes, Part XVI On the Donor Properties of Polynuclear Paracyclophanes and their Sulfur Analogues

Mourad

Hucker

Hopf

1987

Zeitschrift Für Naturforschung B

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Visible, 1H NMR and infrared spectra of the charge-transfer (CT) complexes of polynuclear- [2.2]paracyclophanes and their sulfur analogues as electron donors with 2,3-dichloro-5.6-dicyanobenzoquinone (DDQ ), tetracyanoethylene (TCNE) and 9-dicyanom ethylene-2,4,7-trinitrofluorene (DTF) as π-acceptors have been measured. The data indicate an unexpected high basicity of the polynuclear hydrocarbons relative to their sulfur analogues. The types of CT interactions as well as different factors governing the stability of the CT complexes studied are discussed. The effect of temperature on the CT complexes studied are discussed. The effect of temperature on the CT complexes with TCNE is reported.

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Section: Resultsmentioning

confidence: 99%

“…The cyclophanes 4-7 were prepared by photo chemical ring closure of the appropriate stilbenophanes according to a published procedure [4], The syntheses and spectroscopic properties of these novel aromatic compounds will be published else where [5].…”

Section: Experimental and Physical Measurementsmentioning

confidence: 99%

Molecular Complexes of Cyclophanes, Part XVI On the Donor Properties of Polynuclear Paracyclophanes and their Sulfur Analogues

Mourad

Hucker

Hopf

1987

Zeitschrift Für Naturforschung B

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“…The starting point of our considerations is [2.2](1,4)phenanthrenoparacyclophane (5), [4,5] the parent hydrocarbon of all angularly annelated [2.2]cyclophanes. A five-membered ring may be annelated to its phenanthrene deck in several ways; two such possibilities are shown as 6 and 7 in Scheme 2.…”

Section: Design Of Helical Cyclophane Ligandsmentioning

confidence: 99%

“…[5] At that time we were unable to determine its structure by X-ray crystallography, due to poor crystal quality. However, if this very simple helicenophane were to be used as a building element for larger structures, it would be highly desirable to know its degree of helicity (pitch, deviation of planarity of the phenanthrene ring).…”

Section: Design Of Helical Cyclophane Ligandsmentioning

confidence: 99%

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The Preparation of Helical Cyclophanes Containing Five-membered Rings

et al. 2001

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Oxidative Carbon−Carbon Bond Cleavage of a [2.2]Paracyclophane Derivative − Efficient Intramolecular Trapping of the Radical Cation

et al. 2000

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4‐(2,3,4,5‐Tetraphenyl)phenyl[2.2]paracyclophane (3) has been prepared by cycloaddition of tetracyclone (2) to 4‐ethynyl[2.2]paracyclophane (1). On treatment with FeCl3 or AlCl3 or NOBF4 in nitromethane, 3 undergoes C−C bond cleavage by an electron transfer process to provide the double benzyl radical cation 10. The phenyl groups of the aryl substituent are ideally oriented for intramolecular trapping and, in the presence of the Lewis acids, ring closure to the new phane system 5 takes place in good yield (65%). In the presence of NOBF4, the half‐cyclized aldehyde 6 (66%) is produced. For comparison, [2.2]paracyclophane (7) was also treated with the latter one‐electron oxidant, providing bibenzyl‐4,4′‐dicarbaldehyde (8, 30%) and its monooxime 9 (35%). The structures of the new phane systems 3 and 5 have been determined by X‐ray structural analysis, and the mechanisms leading to these products are discussed.

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Cyclophane series. Part 24. [2.2](1,4)Phenanthrenoparacyclophane: synthesis and two-dimensional proton and carbon-13 NMR study

Cited by 34 publications

References 2 publications

Molecular Complexes of Cyclophanes, Part XVI On the Donor Properties of Polynuclear Paracyclophanes and their Sulfur Analogues

Molecular Complexes of Cyclophanes, Part XVI On the Donor Properties of Polynuclear Paracyclophanes and their Sulfur Analogues

The Preparation of Helical Cyclophanes Containing Five-membered Rings

Oxidative Carbon−Carbon Bond Cleavage of a [2.2]Paracyclophane Derivative − Efficient Intramolecular Trapping of the Radical Cation

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