Reductive Activation of Arenes: XIV. Effect of Medium on the Products Ratio in the Alkylation of Nitrobenzene Radical Anion Sodium Salt

作者: B. A. Selivanov , V. D. Shteingarts

DOI: 10.1023/A:1013969901048

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摘要: The product of nitrobenzene reduction by 1 equiv sodium reacted with tert-butyl iodide in liquid ammonia and its mixtures tetrahydrofuran hexamethylphosphoramide to afford a mixture compounds alkylated either the functional group (N-alkylation) or at benzene ring (C-alkylation). ratio N- C-alkylation products decreases solvents series NH3-THF (5.7) > NH3 (1.0) NH3-HMPA (0.6).

参考文章(9)
Gerald R. Stevenson, Richard C. Reiter, Dean G. Ross, Donald G. Frye, Equilibrium and rate constants for ion association in liquid ammonia The Journal of Physical Chemistry. ,vol. 88, pp. 1854- 1857 ,(1984) , 10.1021/J150653A036
Gerald R. Stevenson, Luis Echegoyen, Luis R. Lizardi, Equilibrium studies by electron spin resonance. II. Nitrobenze free ion-ion pair equilibrium The Journal of Physical Chemistry. ,vol. 76, pp. 2058- 2060 ,(1972) , 10.1021/J100658A027
John F. Garst, Calvin D. Smith, Reactions of alkali benzophenone ketyls with alkyl iodides Journal of the American Chemical Society. ,vol. 98, pp. 1520- 1526 ,(1976) , 10.1021/JA00422A040
Gerald R. Stevenson, Hector Hidalgo, Equilibrium studies by electron spin resonance. III. Nitrobenzene free ion as a hydrogen bond acceptor The Journal of Physical Chemistry. ,vol. 77, pp. 1027- 1030 ,(1973) , 10.1021/J100627A013
F. J. Smentowski, Gerald R. Stevenson, Anion radicals in liquid ammonia Journal of the American Chemical Society. ,vol. 90, pp. 4661- 4662 ,(1968) , 10.1021/JA01019A026
HERMAN STONE, HAROLD SHECHTER, A NEW METHOD FOR THE PREPARATION OF ORGANIC IODIDES Journal of Organic Chemistry. ,vol. 15, pp. 491- 495 ,(1950) , 10.1021/JO01149A008
Peter. Ludwig, Thomas. Layloff, Ralph N. Adams, Solvent Effects on Hyperfine Coupling Constants in Electron Paramagnetic Resonance Spectra Journal of the American Chemical Society. ,vol. 86, pp. 4568- 4573 ,(1964) , 10.1021/JA01075A011