Dimethyl Carbonate as an AmbidentElectrophile

PIETRO TUNDO, LAURA ROSSI, ALESSANDRO LORIS

JOURNAL OF ORGANIC CHEMISTRY

American Chemical Society

Año: 2005 vol. 70 p. 2219 - 2219

0022-3263

font face="NewCenturySchlbk-Roman" size="2"> The features of various anions having different soft/hard character (aliphatic and aromatic amines, alcohoxydes, phenoxides, thiolates) are compared with regard to nucleophilic substitutions on dimethyl carbonate (DMC), using different reaction conditions. Results are well in agreement with the Hard-Soft Acid-Base (HSAB) theory. Accordingly, the high selectivity of monomethylation of CH2 acidic compounds and primary aromatic amines with DMC can be explained by two different subsequent reactions, which are due to the double electrophilic character of DMC. The f