Intramolecular hydrogen bonding between nitro and hydroxy groups in a norbornyl system: a crystallographic and spectroscopic investigation
Abstract
The structure of 3-exo,6-exo-dichloro-5-endo-hydroxy-3-endo-nitrobicyclo[2.2.1]heptane-2-exo-carbonitrile (1a), prepared from 3-endo-nitrobicyclo[2.2.1]hept-5-ene-2-exo-carbonitrile (2) and N-chlorosuccinimide, was elucidated by X-ray crystallography. The compound possesses an intramolecular hydrogen bond between the endo-nitro and hydroxy groups, further evidence for which was obtained from i.r. and n.m.r. spectra.