@article{6d9d55a76697422f9d2c4d8f0856f0af,
title = "A tandem Finkelstein-rearrangement-elimination reaction: a straightforward synthetic route to allyl esters",
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-product of biodiesel industry. The effectiveness of iodine as reagent to hydrolyze allyl esters is also confirmed.",
keywords = "Allylic compounds, Elimination, Esters, Nucleophilic substitution, Rearrangement",
author = "Jordi Eras and Marc Escrib{\`a} and Gemma Villorbina and Mireia Orom{\'i}-Farr{\'u}s and Merc{\`e} Balcells and Ramon Canela",
note = "Funding Information: This work was supported in part by a Grant-in-Aid for the Secretar{\'i}a de Estado de Pol{\'i}tica Cient{\'i}fica y Tecnol{\'o}gica 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'Innovaci{\'o}, Universitats i Empresa de la Generalitat de Catalunya and to the European Social Fund (ESF) for the FI grant of Marc Escrib{\`a} Gelonch. ",
year = "2009",
month = jun,
day = "20",
doi = "10.1016/j.tet.2009.04.042",
language = "English",
volume = "65",
pages = "4866--4870",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Ltd.",
number = "25",
}