Abstract
A catalyst-free, high regio- and chemoselective method is described for the mild conversion of wide varieties of epoxides directly to their corresponding vicinal haloesters using quaternary ammonium halides R4N+X- (X equals; Cl, Br, I; R = n-butyl, n-pentyl, n-hexyl) in the presence of an aliphatic or aromatic carboxylic anhydride at room temperature under neutral and solvent-free conditions.
ACKNOWLEDGMENTS
We gratefully acknowledge the support of this work by the Damghan University Research Council.
Notes
a Molar ratio is related to epoxide: (n-hexyl)4N+Cl-/ Ac2O.
a In all of these reactions, first a mixture of halide salt and carboxylic anhydride was stirred for 15–30 min and then epoxide was added to it.
b Isolated yields.
c Yields are based on NMR analysis.
d The number in parentheses is related to 2-chloro-2-phenylethyl acetate as regioisomeric product.