Effect of carboxylic acids on the metathesis of methyl 10-undecenoate

Balcar, Hynek; Dosedlová, Alena; Matyska, B.

doi:10.1016/0304-5102(87)80114-1

Cited by 9 publications

(2 citation statements)

References 7 publications

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“…6,16 Cross-metathesis of erucic acid with an excess amount of 2-octene in the presence of electrochemically generated active catalyst resulted in the formation of nonfunctionalized hydrocarbon products. Acid-functionalized products were not detected by GC-MS, because of their high boiling points.…”

Section: Resultsmentioning

confidence: 99%

Electrochemically reduced tungsten‐based active species as catalysts for cross‐metathesis reactions: cross‐metathesis of erucic acid with 2‐octene

Çetinkaya

Düz

İmamoǧlu

2003

Applied Organom Chemis

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The cross-metathesis of erucic acid, (CH 3 (CH 2 ) 7 CH CH(CH 2 ) 11 COOH), with an excess of 2-octene in the presence of an electrochemically produced tungsten-based catalyst has been studied. Crossand self-hydrocarbon products, viz. 2-undecene (C 11 ), 6-dodecene (C 12 ) and 6-pentadecene (C 15 ), were detected. The influence of several parameters, such as the 2-octene/erucic acid and 2-octene/catalyst ratios and the reaction time, on the yield of the cross-metathesis product, 6-pentadecene, was studied. The cross-metathesis of functionalized olefins in the presence of an Al-e − -WCl 6 -CH 2 Cl 2 system has not been reported in the literature so far. The cross-metathesis products in the presence of this catalyst system can be obtained with high yield and high specificity.

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Section: Resultsmentioning

confidence: 99%

Electrochemically reduced tungsten‐based active species as catalysts for cross‐metathesis reactions: cross‐metathesis of erucic acid with 2‐octene

Çetinkaya

Düz

İmamoǧlu

2003

Applied Organom Chemis

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“…The dissolution of WCl 6 in acetic acid was proposed as a convenient method for the preparation of mesoporous W 18 O 49 photocatalyst [8]. Spectroscopic evidences indicated that Cl/O interchange and HCl release occurred in the reactions of WCl 6 with controlled amounts of RCO 2 H [R = CH 3 , CH 2 =CH(CH 2 ) 8 , CH 3 (CH 2 ) 10 ], notwithstanding no metal products were isolated [9]. It deserves to be mentioned here that transition metal chlorides, including oxophilic chlorides of metals belonging to the groups 4 [10] and 5 [11], generally react with carboxylic acids affording carboxylato complexes via the release of HCl [12].…”

Section: Introductionmentioning

confidence: 99%

Different outcomes in the reactions of WCl6 with carboxylic acids

et al. 2015

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The reactions of WCl6 with a selection of carboxylic acids were investigated by using dichloromethane as reaction medium. The addition of pyridine-3-carboxylic acid (niacin) to WCl6 gave [C5H4NHC(O)Cl][WOCl5], 1, in 75% yield via selective Cl/O interchange. WCl6 reacted with RCO2H (R = CH3, CBr3, CHCl2) in 1:2 ratio resulting in the formation of HCl and the respective acyl chlorides, RC(O)Cl. WOCl4(κ1-CH3CO2H), 2, was isolated from WCl6/CH3CO2H in 41% yield. The 1:2 reaction of WCl6 with CCl3CO2H proceeded with HCl release affording a mixture of WCl5(O2CCCl3), 3, and WCl4(O2CCCl3)2, 4. Compound 3 was isolated from WCl6/CCl3CO2H (1:1 ratio) in 60% yield. All the metal products were characterized by analytical and spectroscopic techniques. The crystal structure of 1 was ascertained by X-ray diffractometry. DFT calculations were carried out in order to shed light into structural, mechanistic and thermodynamic features

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Reactivity of [WCl6] with Ethers: A Joint Computational, Spectroscopic and Crystallographic Study

et al. 2016

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The reactions of [WCl6] with a series of ethers have been performed in chlorinated solvent and elucidated by means of analytical, spectroscopic and DFT methods. The addition of tetrahydropyran (thp) or 1,4-dioxane to [WCl6] resulted in the reversible formation of the adducts WCl6···L [L = thp (1a), 1,4-dioxane (1b)], detected in solution by NMR spectroscopy. The reaction of [WCl6] with thp in a molar ratio of 1:2 in chloroform at reflux afforded [WOCl4(thp)] (2a), which was isolated in 51 % yield. [WOCl4(OMe2)] (2b) and [WOCl3(OMe2)2] (3a) were isolated in yields of 53 and 18 %, respectively, from the reaction of [WCl6] with an excess of dimethyl ether. [WOCl3(OEt2)2] (3b) was the only identified metal compound produced from the reaction of [WCl6] and OEt2(1:2 molar ratio). According to NMR studies, the oxide ligand in 2a,b and 3a,b was generated by double C–O bond cleavage involving one equivalent of organic reactant. The 1:1 reaction of [WCl6] with 1,2-diethoxyethane led to [WCl5(κ1-OCH2CH2OEt)] (4) and a minor amount of [WCl4(κ2-EtOCH2CH2OEt)] (5). The aryl oxide compound [WCl5(OPh)] (6) was prepared in 62 % yield from the reaction of [WCl6] and anisole by selective Csp3–O bond activation. The prolonged heating of a mixture of [WCl6] and diphenyl ether in 1,2-dichloroethane led to the isolation of the WVcomplex [WCl5(OPh2)] (7). The molecular structures of 2a and 3a were ascertained by X-ray diffraction

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Effect of carboxylic acids on the metathesis of methyl 10-undecenoate

Cited by 9 publications

References 7 publications

Electrochemically reduced tungsten‐based active species as catalysts for cross‐metathesis reactions: cross‐metathesis of erucic acid with 2‐octene

Electrochemically reduced tungsten‐based active species as catalysts for cross‐metathesis reactions: cross‐metathesis of erucic acid with 2‐octene

Different outcomes in the reactions of WCl6 with carboxylic acids

Reactivity of [WCl6] with Ethers: A Joint Computational, Spectroscopic and Crystallographic Study

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