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An example of a novel formation of an oxepin
Author(s) -
Parlow John J.
Publication year - 1995
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.5570320501
Subject(s) - chemistry , ring (chemistry) , intramolecular force , nucleophilic aromatic substitution , nucleophile , fluorine , nucleophilic substitution , tetralone , stereochemistry , medicinal chemistry , organic chemistry , catalysis
A novel formation of an oxepin, namely 9,10,11,12‐tetrafluoro‐5,6‐dihydrobenzo[ b ]naphth[2,1‐ f ]oxepin (5) , starting from pentafluoroacetophenone and 1‐tetralone is described. Also, the same synthesis using 1‐indanone affords a very different ring system namely 1,2,3,4‐tetrafluoro‐5,11b‐dihydro‐7 H ‐benzo[ c ]fluoren‐7‐one (10) . Both synthesis undergo an intramolecular nucleophilic substitution of an ortho ‐fluorine. In one case, the oxygen displaces the fluorine to afford the oxepin 5 and the other a carbon is used as the nucleophile to give the polycyclic ring system 10 .
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