Bromination of endo-7-norbornene derivatives revisited: failure of a computational NMR method in elucidating the configuration of an organic structure

• Demet Demirci Gültekin,
• Arif Daştan,
• Yavuz Taşkesenligil,
• Cavit Kazaz,
• Yunus Zorlu and
• Metin Balci

Beilstein J. Org. Chem. 2023, 19, 764–770, doi:10.3762/bjoc.19.56

• erroneous mechanistic pathway. Keywords: bromination; computational NMR; γ-gauche effect; NMR; NOE-Diff experiments; Introduction Nuclear magnetic resonance (NMR) spectroscopy is one of the most important analytical tools used to determine the structure of organic compounds. NMR not only confirms the

• proof using NOE-Diff experiments: Irradiation at the resonance frequency of the H2 and H3 protons produces a positive NOE for the resonance signal of the bridgehead protons H1 and H4. The fact that only bridgehead protons H1 and H4 give positive NOE clearly indicates that (i) the configuration of the