Nitro-Group-Directed Selective Deacylation and Desulfonation

Abstract

Nitro-substituted phenolic esters and sulfonates were successfully and selectively deacylated and desulfonated, respectively. The directing effect of the nitro group is supported by the excellent regioselectivities and good yields. These reactions demonstrate for the first time that the complexation of AlCl₃ with the phenolic nitro group is stronger than that with the phenolic ester or sulfonate group alone. The mechanism for the selective deacylation and desulfonation directed by the nitro group is proposed.

Key words

selective deacylation - selective desulfonation - nitro group - AlCl₃ - complexation

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