Nitration of pyridine compounds. The reaction of N-nitro-1,4-dihydro-4-pyridinesulfonic acid

Authors
Bakke, JM Riha, J
Citation
Jm. Bakke et J. Riha, Nitration of pyridine compounds. The reaction of N-nitro-1,4-dihydro-4-pyridinesulfonic acid, ACT CHEM SC, 53(5), 1999, pp. 356-359
Citations number
5
Categorie Soggetti
Chemistry
Journal title
ACTA CHEMICA SCANDINAVICA
ISSN journal
0904213X → ACNP
Volume
53
Issue
5
Year of publication
1999
Pages
356 - 359
Database
ISI
SICI code
0904-213X(199905)53:5<356:NOPCTR>2.0.ZU;2-T
Abstract
The reactions of N-nitropyridinium nitrate (1) and 2,6-dideuterio-N-nitropy ridium nitrate (2.6-d(2)-1) with SO(2)xH(2)O-HSO3- have been studied. The r esults are consistent with a reaction scheme in which the formed N-nitro-1, .4-dihydro-4-pyridinesulfonic acid (2) did not react directly to give 3-nit ropyridine but existed in equilibrium with 1 and 2,6-d(2)-1 from which N-ni tro-1,2-dihydro-2-pyridinesulfonic acid (3) was formed. From 3, 3-nitropyri dine was formed by a [1,5] sigmatropic shift of the nitro group.