Nitro-Group–Directed Selective Dealkylation

X Ji, B Cheng, J Song, C Liu, Y Wang

Index: Ji, Xiujie; Cheng, Bowen; Song, Jun; Liu, Chao; Wang, Yufei Synthetic Communications, 2009 , vol. 39, # 11 p. 2053 - 2057

Full Text: HTML

Citation Number: 3

Abstract

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.

Related Articles:

Selective nitration of phenols using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid under aprotic conditions

[Pourali, Ali Reza; Fatemi, Fatemeh Chinese Chemical Letters, 2010 , vol. 21, # 11 p. 1283 - 1286]

Palladium-Catalyzed Hydroxylation of Aryl and Heteroaryl Halides Enabled by the Use of a Palladacycle Precatalyst

[Imoto, Mitsutaka; Matsui, Yasunori; Takeda, Motonori; Tamaki, Akihiro; Taniguchi, Hisaji; Mizuno, Kazuhiko; Ikeda, Hiroshi Journal of Organic Chemistry, 2011 , vol. 76, # 15 p. 6356 - 6361]

Palladium-catalyzed C–O bond formation: direct synthesis of phenols and aryl/alkyl ethers from activated aryl halides

[Chen, Guoshu; Chan, Albert S.C.; Kwong, Fuk Yee Tetrahedron Letters, 2007 , vol. 48, # 3 p. 473 - 476]

Nitration of phenolic compounds by metal-modified montmorillonite KSF

[Tetrahedron, , vol. 61, # 46 p. 10861 - 10867]

A Simple DNase Model System Comprising a Dinuclear Zn (II) Complex in Methanol Accelerates the Cleavage of a Series of Methyl Aryl Phosphate Diesters by 1011− …

[Journal of the American Chemical Society, , vol. 130, # 20 p. 6639 - 6649]

More Articles...