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

…, G Villorbina Noguera, M Oromí Farrús…

Index: Eras, Jordi; Escriba, Marc; Villorbina, Gemma; Oromi-Farrus, Mireia; Balcells, Merce; Canela, Ramon Tetrahedron, 2009 , vol. 65, # 25 p. 4866 - 4870

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Abstract

Abstract 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- ...