Homocoupling of alkyl halides and cyclization of .alpha.,.omega.-dihaloalkanes via activated copper

Ginah, Francis O.; Donovan, Thomas A.; Suchan, Scott D.; Pfennig, Deborah R.; Ebert, Greg W.

doi:10.1021/jo00289a037

Cited by 62 publications

(22 citation statements)

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“…At temperatures above 273 K benzyl cuprates are known to be thermally unstable, giving the respective homocoupled products in good yield. 36 At lower temperatures these organocopper compounds have greater stability but react quickly with benzyl bromide to form the corresponding coupled products. 36 The low melting point of HCl made it possible to detect the reaction products both before (159 K) and after (298 K) defrosting of the sample and to observe unstable organocopper compounds at 298 K reacting with DCl according to:…”

Section: Materials Nanoscience and Catalysismentioning

confidence: 99%

Kinetics and mechanism of the reaction of substituted benzyl bromides with copper in dimethylformamide

Егоров¹,

Matyukhova²,

Анисимов³

2005

Appl. Organometal. Chem.

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The reaction of copper metal with various substituted benzyl bromides in dimethylformamide has been studied and the kinetic and thermodynamic parameters of the reaction have been obtained. Hammett plots of log(k/k • ) vs the substituent constant σ gave good correlations (ρ = 0.24, S ρ = 0.03, r = 0.951). The structure of the organic group has little effect on the rate of reaction of substituted benzyl bromides with copper. In the absence of atmospheric oxygen, oxidative dissolution of copper occurred by the mechanism of single-electron transfer with the formation of 1,2-diphenylethanes and copper(I) complexes. The stereochemistry and intermediate compound were also studied and the reaction mechanism is discussed.

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Section: Materials Nanoscience and Catalysismentioning

confidence: 99%

Kinetics and mechanism of the reaction of substituted benzyl bromides with copper in dimethylformamide

Егоров¹,

Matyukhova²,

Анисимов³

2005

Appl. Organometal. Chem.

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“…At temperatures above 273 K, benzyl cuprates are known to thermally decompose to give their respective homocoupled products in good yield along the elemental copper [36]. At lower temperatures, these organocopper compounds have greater stability but will react quickly with benzyl bromide present to produce the corresponding coupled products [36].…”

mentioning

confidence: 99%

Kinetics and mechanism of the reaction of benzyl bromide with copper in hexamethylphosphoramide

Егоров¹,

Matyukhova²,

Анисимов³

2005

Int J of Chemical Kinetics

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The reaction of copper with benzyl bromides in hexamethylphosphoramide has been studied. The kinetic and thermodynamic parameters of the reaction have been obtained. Hammett plots of log (k/k o ) vs the substituent constant σ gave good correlations (ρ = 0.15, S ρ = 0.02, r = 0.954). The structure of the organic group has little effect on the rate of reaction of benzyl bromide with copper. In the absence of atmospheric oxygen, the oxidative dissolution of copper occurred by the mechanism of single-electron transfer with the formation of 1,2-diphenylethane and copper(I) complexes. The stereochemistry and intermediates compound was also investigated.The reaction mechanism is discussed. C 2005 Wiley Periodicals, Inc. Int J Chem Kinet 37: [296][297][298][299][300][301][302][303][304][305] 2005

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“…Ag n−1 (C 3 H 5 ) + + C 3 H 5 X → Ag n−1 X + + (C 3 H 5 ) 2 (15) Finally in this series, the cluster fragmentation product ion formed in Eq. (7d) undergoes further addition reaction (cf.…”

Section: Subsequent Reactions Arising From the Primary Products Formementioning

confidence: 96%

“…(9b), also undergoes a C C bond coupling reaction with the allyl halide (Eq. (15)) in the case of n = 5 and both X = Br and I (Figs. 2d and 3d).…”

Section: Subsequent Reactions Arising From the Primary Products Formementioning

confidence: 99%

“…One of the most widely studied classes of C C bond coupling reactions are metal mediated reductive coupling of organohalides, the so called "Wurtz" reaction [7]. For example, reductive coupling of allylhalides has been examined with a range of metal species [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] including gas phase iron cations [24] and metal surfaces [25][26][27]. Both silver surfaces [28,29] and silver nano-particles [30] are effective at mediating carbon carbon bond coupling of allyl halides to give 1,5-hexadiene.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Role of cluster size and substrate in the gas phase CC bond coupling reactions of allyl halides mediated by Agn+ and Agn−1H+ cluster cations

Wang

Khairallah

O’Hair

2009

International Journal of Mass Spectrometry

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Homocoupling of alkyl halides and cyclization of .alpha.,.omega.-dihaloalkanes via activated copper

Cited by 62 publications

References 0 publications

Kinetics and mechanism of the reaction of substituted benzyl bromides with copper in dimethylformamide

Kinetics and mechanism of the reaction of substituted benzyl bromides with copper in dimethylformamide

Kinetics and mechanism of the reaction of benzyl bromide with copper in hexamethylphosphoramide

Role of cluster size and substrate in the gas phase CC bond coupling reactions of allyl halides mediated by Agn+ and Agn−1H+ cluster cations

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