A tandem Finkelstein-rearrangement–elimination reaction: a straightforward synthetic route to allyl esters

Use of Crude Glycerol from Biodiesel Producers and Fatty Materials to Prepare Allyl Esters

“…The most important difference between the two heating methods was the reaction time: a total of 96 h was required for the conventional heating conditions, and 3.5 h was required for microwave irradiation. Again these yields were very close to the ones obtained using dichloropropyl fatty esters prepared from fatty acids and pure glycerol [10]. Moreover, they were higher the ones described by Biermann et al [23] using calendula oil or tung oil and allyl alcohol as starting material.…”

“…Sodium thiosulfate allowed us to use a 0.5 molar ratio of sodium iodine to maintain high yields (Table 3). In this case, n-butanol was used as a solvent instead of butanone [10].…”

“…Recently, our research group has described an easy process to obtain allyl esters [10]. These esters were prepared in butanone using a simultaneous Finkelstein rearrangement-elimination reaction of dichloropropyl esters.…”

Carbodeoxygenation of Biomass: The Carbonylation of Glycerol and Higher Polyols to Monocarboxylic Acids

“…[31] Similar observations and formation of allyl acetate have been reported from the reaction of 1,3-dichloro-2-acetyl propane with sodium iodide. [32] Further substitution results in allyl iodide (AI) and addition of DI followed by elimination of I 2 generates propene (P), which undergoes addition of DI to give finally isopropyl iodide (IPI), together with some isopropyl acetate (IPA). Oxidative addition of IPI at rhodium and iridium results in isomerisation to both isopropyl and n-propyl metal complexes, [33] and as a result, the carbonylation of IPI results in the formation of both BA and IBA.…”

Sodium Iodide

“…6 Other applications using sodium iodide as reagent in organic synthesis have been reported. They include the Finkelstein rearrangement-elimination reaction of 2-chloro-1-(chloromethyl)ethyl esters induced by NaI, 7 the DielsAlder reaction between a,a,a′,a′′-tetrabromo-oxylene and 2-cyclopentenone in the presence of NaI, 8 monoiodination of arenes by alkali metal iodide, 9 transformation of azides to primary amines using the CeCl 3 ·7H 2 O/NaI system, 11 and Michael addition of nucleophiles to alkenes promoted by the CeCl 3 ·7H 2 O/NaI system supported on alumina. 12 This document was downloaded for personal use only.…”