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A Novel Aromatic Hydrocarbon with 16π‐Electron Periphery: “Cyclic Bicalicene”
Author(s) -
Yonedo Shigeo,
Shibata Mitsuhiro,
Kida Shuji,
Yoshida Zenichi,
Kai Yasusi,
Miki Kunio,
Kasai Nobutami
Publication year - 1984
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.198400631
Subject(s) - hydrocarbon , electrochemistry , aromatic hydrocarbon , chemistry , electron , aromaticity , polycyclic aromatic hydrocarbon , computational chemistry , photochemistry , molecule , organic chemistry , physics , electrode , nuclear physics
An exception to the Hückel rule in conceivable in the case of the 16π‐electronics species 1 : it reacts, e.g., with N ‐bromosuccinimide with substitution, electrochemical reduction leads to the 18π‐system, and the 1 H‐NMR signals are not shifted to high field. The aromatic stabilization of 1 rests on the resonance of two Kekulé structures and a polarized structure.