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Iron‐Catalyzed Nucleophilic Substitution of Allylic Acetate
Author(s) -
Åkermark Björn,
Sjögren Magnus P. T.
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700372
Subject(s) - chemistry , allylic rearrangement , dimethylamine , morpholine , dichloromethane , catalysis , nucleophilic substitution , substitution reaction , medicinal chemistry , tetrahydrofuran , organic chemistry , nucleophile , ethanol , dimethylformamide , solvent
The combination of diiron nonacarbonyl and dimethylamine gives an active catalyst for displacement of allylic acetate by diethyl methylmalonate. It was found that among a series of amines, only dimethylamine and morpholine were efficient promoters of the reaction. Solvents such as dimethylformamide (DMF) and N ‐methylformamide were much superior to tetrahydrofuran, dichloromethane, and ethanol.