1991
DOI: 10.1002/cjce.5450690141
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Kinetics of the allylation of phenoxide by polyethylene glycol in a two‐phase reaction

Abstract: Polyethylene glycol (PEG) was used as the phase transfer catalyst in the two‐phase allylation of phenoxide with allyl chloride. The kinetics of the reaction both in the organic phase and in the aqueous phase was studied in detail based on the ion‐extraction mechanism. The reaction rates both in the organic and aqueous phases were increased by PEG. The concentration of phenoxide in the organic phase results from adding PEG followed by a reaction second order in the concentration of phenoxide in the aqueous phas… Show more

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Cited by 18 publications
(12 citation statements)
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“…Previous studies [25,26] of the allylation of phenoxide using PEG-400 indicate that the role of PEG-400 is to promote the dissociation of sodium phenoxide in the homogeneous phase reaction, to augment the solubility of sodium phenoxide in the organic phase and to augment the solubility of allyl chloride in the aqueous phase of the two-phase reaction. The free ion of the dissociated phenoxide has been verified as the reactive component in the allylation.…”
Section: Resultsmentioning
confidence: 99%
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“…Previous studies [25,26] of the allylation of phenoxide using PEG-400 indicate that the role of PEG-400 is to promote the dissociation of sodium phenoxide in the homogeneous phase reaction, to augment the solubility of sodium phenoxide in the organic phase and to augment the solubility of allyl chloride in the aqueous phase of the two-phase reaction. The free ion of the dissociated phenoxide has been verified as the reactive component in the allylation.…”
Section: Resultsmentioning
confidence: 99%
“…They concluded that the role of PEG in the homogeneous phase reaction was to promote the dissociation of sodium phenoxide and to enhance the reaction rate. In the two-phase reaction, Wang and Chang [26] also found that the reaction rate, both in the organic phase and in the aqueous phase, was increased by increasing the amount of PEGs. The augmenting of the solubility of sodium phenoxide leads to the increase of the reaction rate in the organic phase and the augmenting of the solubility of allyl chloride in the aqueous phase leads to the increase of the reaction rate in the aqueous phase.…”
Section: Introductionmentioning
confidence: 95%
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“…After many trials, we found that when the reaction was run in the presence of PEG‐400 (15 mol%) as the activated additive and K 2 CO 3 as the base in refluxing MeCN for 5 h [monitored by thin‐layer chromatography (TLC)], the desired 2‐ferrocenoyl‐7‐iodo‐5‐methylbenzo[ b ]furan ( 4b ) was obtained in a good yield of 85%. Presumably, the reaction may be the fact that PEG‐400 could stabilize the transition state , thereby resulting in an increase in the reaction rate. The amount of 15 mol% PEG‐400 was sufficient to push this reaction forward, and more than that amount resulted in a lower yield, which might be because the transition state could be solvated in the larger amount of PEG‐400.…”
Section: Resultsmentioning
confidence: 99%