NOVEL CATALYSIS OF o-NITROPHENYL CARBONATES BY p-DIMETHYLAMINOPYRIDINE

Article abstract of DOI:10.1016/S0040-4039(00)86728-3

Transesterification reactions of o-nitrophenyl carbonates have been found to be greatly facilitated by use of p-dialkylaminopyridines as catalysts.A 20-fold rate increase is observed using 0.01 eq. of p-dimethylaminopyridine in place of 2.00 eq. of triethylamine.Such rate enhancement is not observed with p-nitrophenyl carbonates: 2.00 eq. of Et3N causes reaction to occur 8.5 times faster than 0.01 eq. of DMAP.DMAP catalyzed reactions of o-nitrophenyl carbonate have been used to prepare aromatic carbonates at 0 deg C in high yields, and avoid the necessity of using 2 equiv. of base.