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A Donor‐Acceptor Substituted Quinoid Pentalene
Author(s) -
Sugimoto Toyonari,
Sakai Akihiko,
Takahashi Toshiki,
Ando Hiroshi,
Okuda Tatsushi,
Yoshida Zenichi,
Kai Yasushi,
Kanehisa Nobuko,
Kasai Nobutami
Publication year - 1988
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.198817111
Subject(s) - pentalene , antiaromaticity , acceptor , electron acceptor , chemistry , photochemistry , electron , crystallography , computational chemistry , physics , molecule , organic chemistry , condensed matter physics , aromaticity , quantum mechanics
The title compound is not a Do ⊖ /A ⊕ ‐pentalene but a Do/A‐“pentalenequinone” , as has been shown by an X‐ray structure analysis and the 1 H‐NMR spectrum. Apparently, the formation of this structure is a possibility to circumvent antiaromatic destabilization by the eight π‐electrons of the pentalene. 1 forms stable, blue‐violet crystals of m.p. 220°C.