A tandem Finkelstein-rearrangement-elimination reaction: a straightforward synthetic route to allyl esters |
| |
| Authors: | Jordi Eras Gemma Villorbina Mercè Balcells Ramon Canela |
| |
| Institution: | a Department of Chemistry, Lleida University, 25198 Lleida, Spain
b Centre UdL-IRTA, Lleida University, Rovira Roure 191, 25198 Lleida, Spain |
| |
| 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 |
| 本文献已被 ScienceDirect 等数据库收录！ |
