| Abstract
| - The reaction of 2-chloro-3-nitropyridine with two equivalentsof hydroxide ion was studied by NMR and X-ray crystallography. On the basis of NMR coupling constants, theoriginally formed ring-opened intermediate is the pseudo-cis form, as predicted by the SN(ANRORC) mechanism.However, the first intermediate is unstable and isomerizesto a second intermediate, which was isolated. The pseudo-trans geometry of the second intermediate [3-pentenenitrile,2-nitro-5-oxo, ion(−1), sodium] explains why additional basedoes not lead to the ring-closing reaction as observed with2-chloro-5-nitropyridine.
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