Reactions between 1-chloro-2,4,6-trinitrobenzene and 2-hydroxypyridine, 3-hydroxypyridine, and 4-hydroxypyridine are reported. 4-Hydroxypyridine produces the product of attack at the nitrogen atom, while 3-hydroxypyridine reacts at the oxygen atom. 2-Hydroxypyridine reacts as an ambidentate nucleophile, providing a mixture of products arising from attack at both the oxygen and the nitrogen atom. Reactions between X-substituted-3-hydroxypyridines (X = H, 5-Cl, 6-CH3) and 1-chloro-2,4,6-trinitrobenzene provided 3-pyridinyl 2,4,6-trinitrophenyl ethers, analysed by H-1 and C-13 NMR spectra and by X-ray diffraction. Moderate heating of methanolic solutions of 3-pyridinyl 2,4,6-trinitrophenyl ether and of 6-methyl-3-pyridinyl 2,4,6-trinitrophenyl ether caused a methylation reaction of the pyridine nitrogen ring through trinitroanisole, providing 3-hydroxy-1-methylpyridinium picrate and 1,2-dimethyl-5-hydroxypyridinium picrate. Kinetic data are compared and discussed.

Reactions of Hydroxypyridines with 1-Chloro-2,4,6-trinitrobenzene − Product Structure, Kinetics, and Tautomerism / Carla, Boga; Anna corradi, Bonamartini; Luciano, Forlani; Vincenzo, Modarelli; Righi, Lara; Sgarabotto, Paolo; Paolo edgardo, Todesco. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2001:(2001), pp. 1175-1182. [10.1002/1099-0690(200103)2001:6<1175::AID-EJOC1175>3.0.CO;2-6]

Reactions of Hydroxypyridines with 1-Chloro-2,4,6-trinitrobenzene − Product Structure, Kinetics, and Tautomerism

RIGHI, Lara;SGARABOTTO, Paolo;
2001

Abstract

Reactions between 1-chloro-2,4,6-trinitrobenzene and 2-hydroxypyridine, 3-hydroxypyridine, and 4-hydroxypyridine are reported. 4-Hydroxypyridine produces the product of attack at the nitrogen atom, while 3-hydroxypyridine reacts at the oxygen atom. 2-Hydroxypyridine reacts as an ambidentate nucleophile, providing a mixture of products arising from attack at both the oxygen and the nitrogen atom. Reactions between X-substituted-3-hydroxypyridines (X = H, 5-Cl, 6-CH3) and 1-chloro-2,4,6-trinitrobenzene provided 3-pyridinyl 2,4,6-trinitrophenyl ethers, analysed by H-1 and C-13 NMR spectra and by X-ray diffraction. Moderate heating of methanolic solutions of 3-pyridinyl 2,4,6-trinitrophenyl ether and of 6-methyl-3-pyridinyl 2,4,6-trinitrophenyl ether caused a methylation reaction of the pyridine nitrogen ring through trinitroanisole, providing 3-hydroxy-1-methylpyridinium picrate and 1,2-dimethyl-5-hydroxypyridinium picrate. Kinetic data are compared and discussed.
Reactions of Hydroxypyridines with 1-Chloro-2,4,6-trinitrobenzene − Product Structure, Kinetics, and Tautomerism / Carla, Boga; Anna corradi, Bonamartini; Luciano, Forlani; Vincenzo, Modarelli; Righi, Lara; Sgarabotto, Paolo; Paolo edgardo, Todesco. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2001:(2001), pp. 1175-1182. [10.1002/1099-0690(200103)2001:6<1175::AID-EJOC1175>3.0.CO;2-6]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2468237
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