Polyhalogenonitrobenzenes and derived compounds Part 4. Attempted fluorination of 1,2,3,4-tetrachloro-5,6-dinitrobenzene

Heaton, Alan; Hill, Mark G.; Drakesmith, F. G.

doi:10.1016/s0022-1139(96)03507-5

Cited by 10 publications

(12 citation statements)

References 11 publications

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“…[11,12] The diamines were either commercially www.chemeurj.org available (for 1 and 7) or were synthesised using literature procedures (for 8 and 9). [13][14][15][16] Compound 3 a was obtained from 7 according to the literature procedure. [6] These compounds were very poorly soluble in organic solvents and were, therefore, purified by gradient sublimation under high vacuum.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Ionisation Potentials and Electron Affinities of Hexaazatrinaphthylene Derivatives

Barlow

Zhang

Kaafarani

et al. 2007

Chemistry A European J

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Several hexaazatrinaphthylene derivatives and a tris(thieno)hexaazatriphenylene derivative have been synthesised by reaction of the appropriate diamines with hexaketocyclohexane. The crystal structure of 2,3,8,9,14,15-hexachloro-5,6,11,12,17,18-hexaazatrinaphthylene has been determined by X-ray diffraction; this reveals a molecular structure in good agreement with that predicted by density functional theory (DFT) calculations and pi-stacking with an average spacing between adjacent molecular planes of 3.18 A. Solid-state ionisation potentials have been measured by using UV photoelectron spectroscopy and fall in the range of 5.99 to 7.76 eV, whereas solid-state electron affinities, measured using inverse photoelectron spectroscopy, vary in the range -2.65 to -4.59 eV. The most easily reduced example is a tris(thieno)hexaazatriphenylene substituted with bis(trifluoromethyl)phenyl groups; DFT calculations suggest that the highly exothermic electron affinity is due both to the replacement of the outermost phenylene rings of hexaazatrinaphthylene with thieno groups and to the presence of electron-withdrawing bis(trifluoromethyl)phenyl groups. The rather exothermic electron affinities, the potential for adopting pi-stacked structures and the low intramolecular reorganisation energies obtained by DFT calculations suggest that some of these molecules may be useful electron-transport materials.

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Section: Resultsmentioning

confidence: 99%

“…250 8C) gave fine needle-like microcrystals, which, however, did not give satisfactory elemental analysis. [15,16] (5.00 g, 27.76 mmol) was added to deoxygenated acetic acid (150 mL). The mixture was refluxed for 12 h under nitrogen.…”

Section: 5-bis-(35-bis-trifluoromethylphenyl)-34-dinitro-thiophenmentioning

confidence: 99%

Synthesis, Ionisation Potentials and Electron Affinities of Hexaazatrinaphthylene Derivatives

Barlow

Zhang

Kaafarani

et al. 2007

Chemistry A European J

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“…A Diels–Alder reaction of cyclohexadiene ( 5 ) with ketal 7a furnished exclusively the syn -bis-adduct 8a [ 20 ] which was then converted to the canary-yellow tetraketone 10 by Khan’s original RuCl 3 -catalyzed oxidation protocol [ 21 – 23 ] since Chou’s “optimized” procedure was somewhat capricious in our hands. The twofold condensation with di- or tetrafluoro- o -phenylenediamine ( 12b , c ) [ 24 – 25 ] provided access to the novel fluorinated species 15b – c in acceptable yields (60–70%). This last reaction required harsh conditions and delivered a dark crude product with unspecified tarry material after heating the substrates for several days to 115 °C ( 1 H and 19 F NMR control).…”

Section: Resultsmentioning

confidence: 99%

Preparation, structures and preliminary host–guest studies of fluorinated syn-bis-quinoxaline molecular tweezers

Etzkorn¹,

Timmerman²,

Brooker³

et al. 2010

Beilstein J. Org. Chem.

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SummaryA series of polycyclic frameworks with fluorinated syn-facial quinoxaline sidewalls has been prepared as potential molecular tweezers for electron-rich guest compounds. Our synthetic route to the cyclooctadiene-derived scaffolds 16a–d takes advantage of the facile isolation of a novel spirocyclic precursor 9b with the crucial syn-orientation of its two alkene moieties. The crystal structure of 16c displays two features typical of a molecular tweezer: inclusion of a solvent molecule in the molecular cleft and self-association of the self-complementary scaffolds. Furthermore, host–guest NMR studies of compound 16c in solution show chemical exchange between the unbound and bound electron-rich guest, N,N,N′,N′-tetramethyl-p-phenylenediamine.

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“…Although partially fluorinated N,N-diphenylphenylene-1,2diamine has been prepared, 19 the perfluorinated compound has not, to our knowledge, appeared in the open literature. We prepared N,N-bis-pentafluorophenyl-3,4,5,6-tetrafluorophenylene-1,2-diamine (1) in 49% overall yield using a nucleophilic aromatic substitution strategy 20, 21 from readily available tetrafluorophenylene-1,2-diamine 22 as shown in Scheme 1. Reaction of the starting diamine with two equivalents of n-BuLi at -78 • C in THF gave a bright yellow solution of the doubly deprotonated anilide dianion as confirmed by lowtemperature 1 H and 19 F NMR spectroscopy.…”

Section: Synthesis and Characterization Of Perfluoroarylamine Ligandsmentioning

confidence: 99%

A new weakly coordinating aluminate anion incorporating a chelating perfluoro-bis-anilido ligand

Smith

Piers

et al. 2010

Dalton Trans.

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The synthesis of the fully fluorinated bis-anilido ligand N,N'-bis-pentafluorophenyl-3,4,5,6-tetrafluorophenylene-1,2-diamine, 1 is described. Reaction of one or two equivalents of 1 with AlMe(3) gives aluminium compounds incorporating one or two ligands, the latter being the protonated form of a new weakly coordinating anion (WCA), 3-H. Alternatively, reaction of 1 with LiAlH(4) yields the lithium salt of this anion, 3-Li, which may be employed as a reagent for preparing the trityl and N,N-dimethylanilinium salts of the aluminate anion. All ion pairs are fully characterized and the use of 3-Ph(3)C to generate titanium-based alkyl cations is also described.

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Polyhalogenonitrobenzenes and derived compounds Part 4. Attempted fluorination of 1,2,3,4-tetrachloro-5,6-dinitrobenzene

Cited by 10 publications

References 11 publications

Synthesis, Ionisation Potentials and Electron Affinities of Hexaazatrinaphthylene Derivatives

Synthesis, Ionisation Potentials and Electron Affinities of Hexaazatrinaphthylene Derivatives

Preparation, structures and preliminary host–guest studies of fluorinated syn-bis-quinoxaline molecular tweezers

A new weakly coordinating aluminate anion incorporating a chelating perfluoro-bis-anilido ligand

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