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 1H and 13C 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.
Boga, C., Bonamartini, A.C., Forlani, L., Modarelli, V., Righi, L., Sgarabotto, P., et al. (2001). Reactions of hydroxypyridines with 1-chloro-2,4,6-trinitrobenzene - Product structure, kinetics, and tautomerism. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001(6), 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
Boga C.;Todesco P. E.
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 1H and 13C 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
