STUDIES ON THE SYNTHESIS OF ARYL ETHERS USING ARENE-MANGANESE CHEMISTRY

Selective arylation of polyfunctional phenols, using chlorobenzene- and p-chlorotoluene-manganese tricarbonyl cations, is described. The intermediate arene-manganese complexes are found to undergo stereo- and regioselective reactions with Schollkopf's chiral glycine enolate equivalent to give dienyl-Mn(CO)3 complexes. Treatment of these complexes with N-bromosuccinimide at room temperature, followed by hydrolysis of the dihydropyrazine, gives diaryl ethers in which one of the aromatic rings is an arylglycine methyl ester.