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Cyclohepta[ a ]phenalene: A Highly Electron‐Donating Nonalternant Hydrocarbon
Author(s) -
Sugihara Yoshikazu,
Yamamoto Hiromasa,
Mizoue Kenji,
Murata Ichiro
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198712471
Subject(s) - intramolecular force , benzene , hydrocarbon , ring (chemistry) , chemistry , tetrathiafulvalene , medicinal chemistry , stereochemistry , organic chemistry , molecule
The title compound 1, which forms green needles and can be stored under N 2 at 0°C, is just as easy to oxidize as tetrathiafulvalene. The key step of the synthesis of this first un‐substituted Reid‐hydrocarbon, starting from readily available 1,8‐diiodonaphthalene, is a benzene ring expansion by intramolecular ketocarbene addition. According to the NMR data, compound 1 is best described as a double vinylogous phenylheptafulvalene.
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