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Título:
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A tandem Finkelstein-rearrangement–elimination reaction: a straightforward synthetic route to allyl esters
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Autor/a:
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Eras i Joli, Jordi; Escribà i Gelonch, Marc; Villorbina Noguera, Gemma; Oromí Farrús, Mireia; Balcells Fluvià, Mercè; Canela i Garayoa, Ramon
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Notas:
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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.
This work was supported in part by a Grant-in-Aid for the Secretaría de Estado de Política Científica y Tecnológica of the Spanish Ministry of Education and Culture (Contract grant number: CTQ2006-07451/PPQ). The authors are grateful to the Comissionat per a Universitats i Recerca del Departament d'Innovació, Universitats i Empresa de la Generalitat de Catalunya and to the European Social Fund (ESF) for the FI grant of Marc Escribà Gelonch. |
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Materia(s):
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-Allylic compounds
-Elimination
-Esters
-Nucleophilic substitution
-Rearrangement |
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Derechos:
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(c) Elsevier, 2009
info:eu-repo/semantics/restrictedAccess |
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Tipo de documento:
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article
publishedVersion |
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Editor:
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Elsevier
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Compartir:
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