Bulletin of the Chemical Society of Japan

Direct conversion of arylamines to the halides by deamination with thionitrite or related compounds and anhydrous copper (II) halides.

S Oae, K Shinhama, YH Kim

Index: Oae, Shigeru; Shinhama, Koichi; Kim, Yong Hae Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 4 p. 1065 - 1069

Full Text: HTML

Citation Number: 30

Abstract

Reactions of various arylamines with either t-butyl thionitrite, t-butyl thionitrate, or p- toluenesulfonyl nitrite in the presence of anhydrous copper (II) halides under mild conditions gave corresponding aryl halides in good yields. This reaction in the presence of such olefins as acrylonitrile, styrene, and acrylic acid gave the corresponding 2-aryl-1-haloethanes as the main products. t-Butyl thionitrite, t-butyl thionitrate, and p-toluenesulfonyl nitrite were ...

Related Articles:

Electron-deficient heteroarenium salts: An organocatalytic tool for activation of hydrogen peroxide in oxidations

[Kotoucova, Hana; Strnadova, Iveta; Kovandova, Martina; Chudoba, Josef; Dvorakova, Hana; Cibulka, Radek Organic and Biomolecular Chemistry, 2014 , vol. 12, # 13 p. 2137 - 2142]

Simple and efficient CuI/PEG-400 system for hydroxylation of aryl halides with potassium hydroxide

[Chen, Junmin; Yuan, Tangjun; Hao, Wenyan; Cai, Mingzhong Catalysis Communications, 2011 , vol. 12, # 15 p. 1463 - 1465]

NiCl 2· 6H 2 O/NaBH 4 in methanol: a mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers

[Chouhan, Mangilal; Kumar, Kapil; Sharma, Ratnesh; Grover, Vikas; Nair, Vipin A. Tetrahedron Letters, 2013 , vol. 54, # 34 p. 4540 - 4543]

Synthesis of sulfonic acid functionalized carbon catalyst from glycerol pitch and its application for tetrahydropyranyl protection/deprotection of alcohols and phenols

[Prabhavathi Devi; Gangadhar; Siva Kumar; Shiva Shanker; Prasad; Sai Prasad Journal of Molecular Catalysis A: Chemical, 2011 , vol. 345, # 1-2 p. 96 - 100]

2-(Trimethylsilyl) ethanol as a new alcohol equivalent for copper-catalyzed coupling of aryl iodides

[Dibakar, Mullick; Prakash, Anjanappa; Selvakumar, Kumaravel; Ruckmani, Kandasamy; Sivakumar, Manickam Tetrahedron Letters, 2011 , vol. 52, # 41 p. 5338 - 5341]

More Articles...