Alkyl nitrite-metal halide deamination reactions. 2. Substitutive deamination of arylamines by alkyl nitrites and copper (II) halides. A direct and remarkably efficient …
MP Doyle, B Siegfried, JF Dellaria Jr
Index: Doyle,M.P. et al. Journal of Organic Chemistry, 1977 , vol. 42, p. 2426 - 2431
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Citation Number: 227
Abstract
Alkyl nitrites and anhydrous copper(I1) halides rapidly convert arylamines into aryl chlorides and bromides in high yield. One molar equivalent of alkyl nitrite and 0.5 molar equiv of copper(I1) chloride or bromide are required for this direct substitutive deamination reaction, which results in the production of cupric oxide, nitrogen, and alco- hol as well as aryl halide. Reactions of copper(I1) halides and tert -butyl nitrite in acetonitrile with 15 representative arylamines ...
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