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[2.2](1,4)Benzo[ g ]chrysenoparacyclophane Dianion: A Novel, Paratropic, Double‐Layered Carbanion
Author(s) -
Frim Ron,
Rabinovitz Mordecai,
Hopf Henning,
Hucker Joachim
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.198702321
Subject(s) - carbanion , benzene , chemistry , ring (chemistry) , stereochemistry , hydrocarbon , medicinal chemistry , organic chemistry
A novel through‐space interaction between a polycyclic charged 4nπ‐electron system and a phane like coupled benzene ring could be observed in the title compound 1 . This interaction manifests itself in particular in the extreme downfield shifts of the signals of the H c and H d protons (M Na, Li). The synthesis of the hydrocarbon precursor of 1 was achieved in few steps from commercially available [2.2]paracyclophane.
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