Crystal structures of thetrans-cyclooctene complexes of copper(I) chloride and silver nitrate

Rencken, Ilmarie; Boeyens, Jan C. A.; Orchard, S. W.

doi:10.1007/bf01194320

Cited by 7 publications

(5 citation statements)

References 26 publications

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“…The Cu−O bond distances are in the range 1.963(4)−1.983(4) Å. The Cu−C bond lengths range from 2.031(5) to 2.043(5) Å to be compared to the values of 2.024(6)−2.074(6) Å observed in the copper(I) derivative catena -Cu(μ-Cl)(coe) 1 View of the molecular structure of [Cu(μ - CF 3 COO)(coe)] 2 with the atomic numbering scheme. 1 Selected Bond Distances (Å) and Angles (deg) in [Cu(μ - CF 3 COO)(coe)] 2 a Cu(1)−M(1) 1.919(5) Cu(2)−M(2) 1.921(5) Cu(1)−C(5) 2.043(5) Cu(2)−C(13) 2.038(5) Cu(1)−C(6) 2.031(5) Cu(2)−C(14) 2.037(5) Cu(1)−O(1) 1.964(4) Cu(2)−O(2) 1.963(4) Cu(1)−O(4) 1.973(4) Cu(2)−O(3) 1.983(4)O(1)−Cu(1)−O(4) 103.54(17) O(2)−Cu(2)−O(3) 102.10(16) O(1)−Cu(1)−M(1) 128.64(16) O(2)−Cu(2)−M(2) 129.06(16) O(4)−Cu(1)−M(1) 126.15(16) O(3)−Cu(2)−M(2) 128.55(19) a M(1) and M(2) are the midpoints of the C(5)−C(6) and C(13)−C(14) double bonds.

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confidence: 99%

Olefin Trifluoroacetato Derivatives of Copper(I) and Their Olefin/CO Exchange Reactions

et al. 2005

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Compounds of the general formula Cu(CF3COO)(olefin) (olefin = cyclooctene (coe), 1,5-cyclooctadiene (cod), diethylfumarate (defu), methylcinnamate (meci)) have been prepared, and the molecular structures have been solved by X-ray diffraction for olefin = coe, defu, meci. The complexes feature a dimeric [Cu2(μ-CF3COO)2(olefin)2] core with bridging trifluoroacetates and a η2-bonded olefin. In the case of the defu and meci complexes, [Cu2(μ-CF3COO)2(olefin)2] dimeric units are linked by the oxygen atom of a carbonyl group of the ester to give polymeric chains. The compound [Cu2(μ-CF3COO)2(meci)2] n is the first structurally characterized example of a metal-bonded methylcinnamate. By recrystallization of [Cu2(CF3COO)2(cod)2], a derivative featuring a cod/Cu molar ratio of 0.5 has been isolated and structurally characterized as [Cu2(μ-CF3COO)2(μ-cod)] n , which represents the first example of a polymeric metal complex containing a bridging cod ligand. The carbonylation reaction of [Cu(CF3COO)(olefin)]2 (olefin = coe, cod, defu; 2Cu(CF3COO)(olefin) + 2CO ⇄ [Cu(CF3COO)(CO)]2 + 2(olefin)) has been studied gas volumetrically, and the equilibrium constants are 12.6 ± 2.4 M-1 (298.3 K, cod), (6.3 ± 3.2) × 102 M-1 (293.2 K, coe), and (1.1 ± 0.7) × 107 M-1 (293.2 K, defu). The enthalpy changes, obtained from variable-temperature experiments, are −46 ± 4 (olefin = cod), −71 ± 17 (coe), and −112 ± 20 kJ mol-1 (defu). These data for copper(I) are compared with those obtained for the 3d3 V(II) and 5d10 Au(I) systems VCp2(CO) and AuCl(CO).

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…”

Section: Resultsmentioning

confidence: 99%

Olefin Trifluoroacetato Derivatives of Copper(I) and Their Olefin/CO Exchange Reactions

et al. 2005

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“…A white foam formed after 18–20 h at the interface of the phases in the extraction module when performing the reaction with ( Z )‐ 5 . The white foam was the ( E )‐ 5 −Ag(I) complex (likely [( E )‐ 5 −AgNO 3 ]) according to analysis by 1 H NMR. It was hypothesized that the precipitation of this white solid was caused by saturation of the aqueous phase with the ( E )‐ 5 −Ag(I) complex, which was insoluble in heptane .…”

Section: Resultsmentioning

confidence: 99%

Rapid Production of trans‐Cyclooctenes in Continuous Flow

Blanco‐Ania¹,

Maartense²,

Rutjes³

2018

ChemPhotoChem

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A new method for rapid larger‐scale production of trans‐cyclooctenes (TCOs) in continuous flow was developed: Up to 2.2 g/h of specific TCOs can be produced by using this procedure. This method utilizes the classical photoisomerization of cis‐cyclooctenes (CCOs) for the synthesis of TCOs but substitutes the conventionally used silver nitrate impregnated silica gel column for a liquid−liquid extraction module. In addition, this method provides the possibility of external addition of a substrate to scale up and speed up the production of TCOs because the concentration of the CCO is kept constant. This method was applied for the synthesis of several commonly used TCOs.

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“…Previously, a crystal structure showed that trans -cyclooctene coordinates with AgNO 3 as a 1 : 1 complex. 60 X-ray quality crystals of silver complex 2a were grown from ethyl acetate/methanol. Selected bond lengths and angles are displayed in Fig.…”

Section: Resultsmentioning

confidence: 99%

Photochemical syntheses, transformations, and bioorthogonal chemistry oftrans-cycloheptene and silatrans-cycloheptene Ag(i) complexes

et al. 2018

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Crystal structures of thetrans-cyclooctene complexes of copper(I) chloride and silver nitrate

Cited by 7 publications

References 26 publications

Olefin Trifluoroacetato Derivatives of Copper(I) and Their Olefin/CO Exchange Reactions

Olefin Trifluoroacetato Derivatives of Copper(I) and Their Olefin/CO Exchange Reactions

Rapid Production of trans‐Cyclooctenes in Continuous Flow

Photochemical syntheses, transformations, and bioorthogonal chemistry oftrans-cycloheptene and silatrans-cycloheptene Ag(i) complexes

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