Reactions of copper(II) halides with aromatic compounds—XI

Mancilla, Jerson; Nonhebel, D. C.; Russell, J.A.

doi:10.1016/0040-4020(75)80155-4

Cited by 8 publications

(3 citation statements)

References 14 publications

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“…A similar conversion has been reported previously in the literature, in which a series of 9‐alkyl‐ and aryl‐anthracenes reacted with copper(II) bromide in methanol, via a mechanism involving several steps of electron‐transfer oxidation and addition of methanol, to give 10‐alkyl (or aryl)‐10‐methoxyanthrones as the major product 7. In the present work, it seems that the presence of CuBr 2 and methanol promoted the reaction of anthracene to the anthronyl ligand in 2a and 2b .…”

Section: Resultssupporting

confidence: 80%

“…When a ligand containing fluorescent units coordinates to metal ions, especially copper(II), its fluorescence properties may change significantly 8. We studied the solid‐state fluorescence of ligand L and complex 1 at room temperature (Figure 5; complexes 2a and 2b were not measured because the fluorescent unit was destroyed in the ligand L′ 7). The ligand L showed a visible emission maximum at 463 nm upon excitation at 326 nm which is characteristic of anthracene.…”

Section: Resultsmentioning

confidence: 99%

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Copper(II) Complexes with N‐(9‐anthracenyl)‐N′‐(3‐pyridyl)urea (L) and a Derivative of L: Synthesis, Structure, and Fluorescent Properties

Zhao

Xiao

Jia

et al. 2010

Zeitschrift anorg allge chemie

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Three copper(II) complexes, [Cu2(OAc)4L2]·2CH3OH (1), [CuBr2L′2(CH3OH)]·CH3OH (2a), and [CuBr2L′2(DMSO)]·0.5CH3OH (2b) {L = N‐(9‐anthracenyl)‐N′‐(3‐pyridyl)urea and L′ = N‐[10‐(10‐methoxy‐anthronyl)]‐N′‐(3‐pyridyl)urea} have been synthesized by the reaction of L with the corresponding copper(II) salts. Complex 1 shows a dinuclear structure with a conventional “paddlewheel” motif, in which four acetate units bridge the two CuII ions. In complexes 2a and 2b, the anthracenyl ligand L has been converted to an anthronyl derivative L′, and the central metal ion exhibits a distorted square pyramidal arrangement, with two pyridyl nitrogen atoms and two bromide ions defining the basal plane and the apical position is occupied by a solvent molecule (CH3OH in 2a and DMSO in 2b).

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Section: Resultssupporting

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Copper(II) Complexes with N‐(9‐anthracenyl)‐N′‐(3‐pyridyl)urea (L) and a Derivative of L: Synthesis, Structure, and Fluorescent Properties

Zhao

Xiao

Jia

et al. 2010

Zeitschrift anorg allge chemie

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“…The IR spectra were recorded on a Perkin-Elmer 1420 infrared spectrophotometer. The known ethers 1a ,20a 7a ,20f and 7b ,20g dimers 3a ,20b 3b ,20c and 4a , and chlorides 6a 20d and 6b 20c were prepared according to reported procedures. Chloride 9b was identified by comparison of 1 H NMR data.…”

Section: Methodsmentioning

confidence: 99%

Multiple-Photon Chemistry of 9-(Phenoxymethyl)- and 9,10-Bis(phenoxymethyl)anthracenes in the Laser-Jet: Generation, Photochemistry, and Time-Resolved Laser-Flash Spectroscopy of Anthracenylmethyl Radicals and Pulse Radiolysis of 9-(Bromomethyl)anthracene

et al. 1997

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In the high-intensity laser-jet (LJ) photolysis of 9-(phenoxymethyl)anthracene (1a) and 9,10-bis(phenoxymethyl)anthracene (1b) multiple-photon chemistry was observed. Thus, while the [4 + 4] photodimer 8a was formed as the one-photon product in the low-intensity conventional photolysis of monoether 1a, the high-intensity irradiation in the laser-jet yielded 1,2-bis(9-anthracenyl)ethane (3a), lepidopterene (4a), biplanene (5a), 9-(chloromethyl)anthracene (6a), and 9-(methoxymethyl)anthracene (7a) as main products. The product distribution depended on the solvent used: after C−O homolysis of the ether 1a, for which at least two photons are required, the resulting arylmethyl radical 2a dimerizes in benzene, in methylene chloride it engages in photoinduced electron transfer, while in methanol it undergoes photoionization. With the help of time-resolved laser-flash photolysis of the monoether 1a it was confirmed that the homolysis of the C−O bond leads to the 9-anthracenylmethyl radical 2a. The authentic radical 2a was generated independently by time-resolved pulse radiolysis and laser-flash photolysis of 9-(bromomethyl)anthracene. Analogous to the monoether 1a, the bisether 1b gave under the high intensity conditions of the laser-jet irradiation tetrabenzo[2.2]paracyclophane (3b), its photodimer (5b), 9,10-(bischloromethyl)anthracene (6b), and 9-(chloromethyl)-10-(phenoxymethyl)anthracene (9b); their distribution depended also on the solvent used. Mechanistic pathways are offered for these multiple-photon processes.

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ChemInform Abstract: REACTIONS OF COPPER(II) HALIDES WITH AROMATIC COMPOUNDS. XI. REACTIONS OF 9‐ALKYL‐ AND 9‐ARYLANTHRACENES IN METHANOL

Mancilla¹,

Nonhebel²,

Russell³

1976

Chemischer Informationsdienst

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Reactions of copper(II) halides with aromatic compounds—XI

Cited by 8 publications

References 14 publications

Copper(II) Complexes with N‐(9‐anthracenyl)‐N′‐(3‐pyridyl)urea (L) and a Derivative of L: Synthesis, Structure, and Fluorescent Properties

Copper(II) Complexes with N‐(9‐anthracenyl)‐N′‐(3‐pyridyl)urea (L) and a Derivative of L: Synthesis, Structure, and Fluorescent Properties

Multiple-Photon Chemistry of 9-(Phenoxymethyl)- and 9,10-Bis(phenoxymethyl)anthracenes in the Laser-Jet: Generation, Photochemistry, and Time-Resolved Laser-Flash Spectroscopy of Anthracenylmethyl Radicals and Pulse Radiolysis of 9-(Bromomethyl)anthracene

ChemInform Abstract: REACTIONS OF COPPER(II) HALIDES WITH AROMATIC COMPOUNDS. XI. REACTIONS OF 9‐ALKYL‐ AND 9‐ARYLANTHRACENES IN METHANOL

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