Tetrahedron Letters p. 1739 - 1742 (1982)
Update date:2022-08-04
Topics:
Brunelle, Daniel J.
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.
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