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Furan derivatives. Part 9 . Synthesis and properties of cyclohepta[ cd ]benzofurans
Author(s) -
Horaguchi Takaaki,
Tanemura Kiyoshi,
Suzuki Tsuneo
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.5570250106
Subject(s) - chemistry , furan , benzofuran , acetic anhydride , ring (chemistry) , protonation , double bond , acetonitrile , medicinal chemistry , acylation , acetic acid , organic chemistry , carbon fibers , triple bond , catalysis , ion , materials science , composite number , composite material
Abstract Cyclohepta[ cd ]benzofurans 1a‐c were synthesized by heating (5‐oxo‐5 H ‐benzocyclohepten‐4‐yloxy)acetic acids 7a‐c with sodium acetate in acetic anhydride or by irradiation of 7a‐c in acetonitrile. Several reactions such as protonation, catalytic hydrogenation, Diels‐Alder reaction, acylation, and photoreaction were examined for 1a‐b . The results show that cyclohepta[ cd ]benzofurans have both properties of heptafulvene and benzofuran. The carbon‐carbon double bond in the furan ring of 1a has aromatic character, however, the carbon‐carbon double bonds in the seven‐membered ring have olefinic character.