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Reaction of 5 H ‐dibenz[ b,f ]azepine with t ‐butyl hypochlorite: An aromatic nitrenium ion intermediate?
Author(s) -
Cann Michael C.,
Lezinsky David
Publication year - 1988
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.5570250331
Subject(s) - chemistry , azepine , hypochlorite , ion , medicinal chemistry , reaction mechanism , organic chemistry , catalysis
The reaction of 5 H ‐dibenz[ b,f ]azepine with t ‐butyl hypochlorite and this same reaction in the presence of silver(I) were studied in an attempt to generate dibenz[ b,f ]azatropylium, an aromatic nitrenium ion. Analysis of the product mixture from this reaction mitigate against formation of this ion. An alternate mechanism is presented.