dc.contributor.author |
Eras i Joli, Jordi |
dc.contributor.author |
Escribà i Gelonch, Marc |
dc.contributor.author |
Villorbina Noguera, Gemma |
dc.contributor.author |
Oromí Farrús, Mireia |
dc.contributor.author |
Balcells Fluvià, Mercè |
dc.contributor.author |
Canela i Garayoa, Ramon |
dc.date |
2016-11-04T08:42:40Z |
dc.date |
2009 |
dc.date |
10000-01-01 |
dc.identifier |
0040-4020 |
dc.identifier |
http://hdl.handle.net/10459.1/58377 |
dc.identifier |
https://doi.org/10.1016/j.tet.2009.04.042 |
dc.identifier.uri |
http://hdl.handle.net/10459.1/58377 |
dc.description |
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. |
dc.description |
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. |
dc.language |
eng |
dc.publisher |
Elsevier |
dc.relation |
MIECI/PN2004-2007/CTQ2006-07451/PPQ |
dc.relation |
Reproducció del document publicat a https://doi.org/10.1016/j.tet.2009.04.042 |
dc.relation |
Tetrahedron, 2009, vol. 65, núm. 25, p. 4866–4870 |
dc.rights |
(c) Elsevier, 2009 |
dc.rights |
info:eu-repo/semantics/restrictedAccess |
dc.subject |
Allylic compounds |
dc.subject |
Elimination |
dc.subject |
Esters |
dc.subject |
Nucleophilic substitution |
dc.subject |
Rearrangement |
dc.title |
A tandem Finkelstein-rearrangement–elimination reaction: a straightforward synthetic route to allyl esters |
dc.type |
article |
dc.type |
publishedVersion |