Synthesis 2006(15): 2478-2482  
DOI: 10.1055/s-2006-942451
PAPER
© Georg Thieme Verlag Stuttgart · New York

Nitro-Group-Directed Selective Deacylation and Desulfonation

Xiujie Ji, Chunbao Li*
Department of Chemistry, Tianjin University, Tianjin 300072, P. R. of China
Fax: +86(22)27403475; e-Mail: lichunbao@tju.edu.cn;
Further Information

Publication History

Received 14 February 2006
Publication Date:
28 June 2006 (eFirst)

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.

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