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7701414 
Journal Article 
Reactions of hydroxypyridines with 1-chloro-2,4,6-trinitrobenzene - Product structure, kinetics, and tautomerism 
Boga, C; Bonamartini, AC; Forlani, L; Modarelli, V; Righi, L; Sgarabotto, P; Todesco, PE; , 
2001 
Yes 
European Journal of Organic Chemistry
ISSN: 1434-193X
EISSN: 1099-0690 
WILEY-V C H VERLAG GMBH 
WEINHEIM 
1175-1182 
WOS:000167553000020 
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.