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The mechanism of the chapman rearrangement of N ‐arylbenzimidate on the basis of the molecular structure established by X‐ray. Part II
Author(s) -
Kimura Michio,
Okabayashi Ichizo,
Isogai Koji
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.5570250153
Subject(s) - chemistry , acridine , yield (engineering) , stereochemistry , mechanism (biology) , rearrangement reaction , basis (linear algebra) , reaction mechanism , computational chemistry , organic chemistry , geometry , thermodynamics , physics , mathematics , catalysis , philosophy , epistemology
Dibenz[ c,h ]acridine ( 13 ) was formed directly by the Chapman rearrangement of 2‐methoxycarbonyl‐1‐naphthyl‐ N ‐1′‐naphthylbenzimidate ( 11 ) without isolation of intermediate 12 . When the Chapman rearrangement was carried out under mild reaction conditions, the intermediate 12 was isolated in high yield, whose structure was determined by the X‐ray studies. The mechanism of the Chapman rearrangement can be interpreted on the basis of the X‐ray data of 11 and 12 .