Nitro-Group–Directed Selective Dealkylation

Xiujie Ji Tianjin Municipal Key Laboratory of Fiber Modification and Functional Fiber, School of Material Science and Chemical Engineering, Tianjin Polytechnic University, Tianjin, China

Bowen Cheng Tianjin Municipal Key Laboratory of Fiber Modification and Functional Fiber, School of Material Science and Chemical Engineering, Tianjin Polytechnic University, Tianjin, ChinaCorrespondence[email protected]

Jun Song Tianjin Municipal Key Laboratory of Fiber Modification and Functional Fiber, School of Material Science and Chemical Engineering, Tianjin Polytechnic University, Tianjin, China

Chao Liu School of Materials Science and Engineering, Hebei University of Technology, Tianjin, China

Yufei Wang School of Chemical Engineering, Dalian University of Technology, Dalian, China

Abstract

Nitro-substituted phenolic ethers were successfully selectively dealkylated. The directing effect of the nitro group is supported by the excellent regioselectivities and good yields. These reactions demonstrate that the complexation of AlCl₃ with the phenolic nitro group is stronger than with the phenolic ether alone. The mechanism for the selective dealkylation directed by the nitro group is proposed.

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Notes

^aYield of isolated product.

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Nitro-Group–Directed Selective Dealkylation

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Nitro-Group–Directed Selective Dealkylation

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