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Electrophilic substitution of dibenz[ b,f ]oxepin
Author(s) -
Bavin P. M. G.,
Bartle K. D.,
Jones D. W.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050304
Subject(s) - chemistry , nitration , electrophilic substitution , bromine , electrophilic aromatic substitution , medicinal chemistry , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry
Dibenz[ b,f ]oxepin undergoes nitration and acid‐catalyzed deuteration at the 10‐position and adds bromine across the 10,11 bond. These reactions contradict predictions made by the SCFMO method. Chemical reactions and NMR spectroscopy suggest that dibenz[ b,f ]oxepin is only weakly aromatic.