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Synthesis and Unusual NMR‐Spectroscopic Behavior of a Strained Bicyclic Ammonium Salt
Author(s) -
Pusch Stefan,
Schollmeyer Dieter,
Opatz Till
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701594
Subject(s) - chemistry , bicyclic molecule , salt (chemistry) , ammonium , pyridine , nuclear magnetic resonance spectroscopy , crystallography , inorganic chemistry , stereochemistry , medicinal chemistry , organic chemistry
The first synthesis of a 2‐azabicyclo[2.2.0]hexenium salt is described. It is available from pyridine in four steps. This strained bicyclic ammonium salt was characterized by 1 H, 13 C, and 2D NMR spectroscopy as well as by XRD. Due to its unusual NMR spectroscopic characteristics, DFT calculations were performed to additionally support the proposed structure. The strained cation shows significant hyperconjugative stabilization.