- [Pd(μ-Br)(PtBu3)]2 as a highly active isomerization catalyst: Synthesis of enol esters from allylic esters
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The dimeric Pd(I)-complex [Pd(μ-Br)(PtBu3)] 2 was found to be highly active for catalyzing double-bond migration in various substrates such as unsaturated ethers, alcohols, amides, and arenes, under mild conditions. It efficiently mediates the conversion of allylic esters into enol esters, rather than inserting into the allylic C-O bond. The broad applicability of this reaction was demonstrated with the synthesis of 22 functionalized enol esters.
- Mamone, Patrizia,Gruenberg, Matthias F.,Fromm, Andreas,Khan, Bilal A.,Goossen, Lukas J.
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supporting information; experimental part
p. 3716 - 3719
(2012/09/08)
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- A tandem Finkelstein-rearrangement-elimination reaction: a straightforward synthetic route to allyl esters
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Allyl esters can be obtained by a Finkelstein-rearrangement-elimination reaction of 2-chloro-1-(chloromethyl)ethyl esters induced by NaI. Sodium iodide can be used below equivalence using a reductive agent as sodium thiosulfate. High yields are obtained with most of the diverse esters studied. The method described avoids the use of allyl alcohol as a reagent. 2-Chloro-1-(chloromethyl)ethyl esters are prepared from glycerol, the main by-product of biodiesel industry. The effectiveness of iodine as reagent to hydrolyze allyl esters is also confirmed.
- Eras, Jordi,Escribà, Marc,Villorbina, Gemma,Oromí-Farrús, Mireia,Balcells, Mercè,Canela, Ramon
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experimental part
p. 4866 - 4870
(2009/10/02)
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- Synthesis of allyl esters of fatty acids and their ovicidal effect on Cydia pomonella (L.)
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Eight allyl esters of fatty acids were synthesized in moderate to high yields with a novel two-step procedure using glycerol as a starting material. The two-step methodology avoids the use of allyl alcohol. The first step consisted of heating at 80 °C for 48 h a 2:1:5 mmol mixture of glycerol, a fatty acid, and chlorotrimethylsilane in a solvent-free medium. The crude compound was then dissolved in butanone and heated at 115 °C in the presence of Nal. A tandem Finkelstein rearrangement-elimination reaction occurs, producing the corresponding allyl ester. The activity of these esters against Cydia pomonella (L.) (Lepidoptera: Tortricidae) eggs was tested in the laboratory by topical application of one 0.1 μL drop. All of the compounds showed a concentration-mortality response and caused 100% mortality at the highest concentration tested (10 mg/mL). There was an inverse relationship between the alkyl chain length and the ovicidal activity of the allyl ester; the LC50 and the LC90 of the two compounds that have the longer alkyl chains were significantly higher than those of the rest of the compounds. The ovicidal and IGR activities of this kind of compound appear to be unprecedented.
- Escriba, Marc,Barbut, Montserrat,Eras, Jordi,Canela, Ramon,Avilla, Jesus,Balcells, Merge
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experimental part
p. 4849 - 4853
(2010/06/14)
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- A Simple and Efficient Esterification Method
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A convenient and practical esterification was realized and this reaction proceeded without a dehydrating reagent or water removal equipment. The synthesis of esters by reaction of carboxylic acids with various alcohols such as methyl, ethyl, isopropyl, isobutyl, allyl, benzyl, propargyl and decanyl alcohols were achieved with a catalytic amount of CBr4 under refluxing reaction condition.
- Ming-Yi, Chen,Lee, Adam Shih-Yuan
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p. 103 - 108
(2007/10/03)
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