A. Bomben, C. Marques, M. Selva
Oct 16, 1995
Citations
0
Influential Citations
29
Citations
Journal
Tetrahedron
Abstract
Abstract A one-pot procedure for the mono-C-methylation of methyl aryloxyacetates and aryloxyaceto nitnles by dimethyl carbonate (DMC) is reported The reaction is earned out in an autoclave at high temperatures (180–200 ° C) and in the presence of a base (K 2 CO 3 or bart -BuOK). Although DMC is used either as the alkylating agent or as the solvent (30 molar excess with respect to the substrates). The selectivity towards the mono-methylated products (methyl 2-aryloxypropionates and 2-aryloxypropio nitnles, respectively) is typically up to 99%, at complete conversion; no dialkylated by-products form. The reasons of such an unusual behaviour is explained by a mechanism involving an initial carboxymethylation followed by a methylation reaction.