- In situ synthesis of 2-allyloxy-1-methylpyridinium triflate for the allylation of carboxylic acids
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2-Allyloxypyridinium triflate is formed in situ by treating a mixture of 2-allyloxypyridine, a carboxylic acid, and toluene with methyl triflate. Subsequent warming of the reaction mixture in the presence of potassium carbonate leads to efficient formation of allyl esters in good to excellent yields.
- Strayer, Timothy A.,Culy, Caleb C.,Bunner, Matthew H.,Frank, Amie R.,Albiniak, Philip A.
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supporting information
p. 6807 - 6809
(2016/01/26)
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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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- Scandium triflate catalyzed transesterification of carboxylic esters
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The direct transesterification of carboxylic esters is efficiently catalyzed with Sc(OTf)3 (10 mol%) in boiling alcoholic solvent. Methyl, ethyl, isopropyl, and allyl esters were prepared from a broad range of different substrates in high yields. The application of microwave irradiation led to significantly reduced reaction times. Georg Thieme Verlag Stuttgart.
- Remme, Nicole,Koschek, Katharina,Schneider, Christoph
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p. 491 - 493
(2007/12/27)
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- Enzymatic removal of carboxyl protecting groups. III. Fast removal of allyl and chloroethyl esters by Bacillus subtilis esterase (BS2)
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(Chemical Equation Presented) An esterase from Bacillus subtilis (BS2) allows the fast and selective removal of allyl, 2-chloroethyl, and 2,2,2-chloroethyl esters under mild conditions in high yields. In addition, BS2 easily hydrolyzes phenacyl esters, while the hydrolysis of sterically hindered diphenylmethyl esters is slow, requiring longer reaction time and higher enzyme/substrate ratio.
- Fotakopoulou, Irene,Barbayianni, Efrosini,Constantinou-Kokotou, Violetta,Bornscheuer, Uwe T.,Kokotos, George
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p. 782 - 786
(2007/10/03)
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