Protonation‐Induced Cyclocondensation of 1‐Aryl Ethynylanthraquinones: Expanding the π Conjugation | Zendy

Kondo Mio | Zendy; Uchikawa Maai | Zendy; Zhang WenWei | Zendy; Namiki Kosuke | Zendy; Kume Shoko | Zendy; Murata Masaki | Zendy; Kobayashi Yoshio | Zendy; Nishihara Hiroshi | Zendy

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Protonation‐Induced Cyclocondensation of 1‐Aryl Ethynylanthraquinones: Expanding the π Conjugation

Author(s) -

Kondo Mio,

Uchikawa Maai,

Zhang WenWei,

Namiki Kosuke,

Kume Shoko,

Murata Masaki,

Kobayashi Yoshio,

Nishihara Hiroshi

Publication year - 2007

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200701766

Subject(s) - intramolecular force , protonation , aryl , chemistry , electron transfer , derivative (finance) , proton , combinatorial chemistry , stereochemistry , photochemistry , organic chemistry , physics , nuclear physics , ion , alkyl , financial economics , economics

Just add a proton : The cyclocondensation of 1‐aryl ethynylanthraquinones in the presence of a strong organic acid proceeds almost quantitatively to give oxodihydrodibenzochromenylium compounds (see scheme for a 1‐ferrocenyl derivative; blue C, red O, purple Fe). Expansion of the π‐conjugated system of the starting anthraquinones causes a lowering of the π* orbital and promotes intramolecular electron transfer.

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