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Synthesis and Properties of Vinylogous 6‐(Cyclopentadienyl)pentafulvenes
Author(s) -
Eiermann Matthias,
Stowasser Bernd,
Hafner Klaus,
Bierwirth Klaus,
Frank Anette,
Lerch Alexander,
Reußwig Jürgen
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230636
Subject(s) - chemistry , cyclopentadienyl complex , alkali metal , cyanine , heteroatom , cyclic voltammetry , salt (chemistry) , nuclear magnetic resonance spectroscopy , metal , inorganic chemistry , polymer chemistry , medicinal chemistry , stereochemistry , organic chemistry , ring (chemistry) , electrochemistry , catalysis , fluorescence , electrode , physics , quantum mechanics
The application of the principle of kinetic stabilization on vinylogous 6‐(cyclopentadienyl)pentafulvenes 1 led to the synthesis of the di‐ and tetra‐ tert ‐butyl derivatives 7a – e and 8a ‐ c . Their reactions with bases and acids form charged, heteroatom‐free cyanine‐type carbanionic 9a ‐ e, 10a – e and carbocationic ll a – e, 12a – c species which were characterized with NMR and UV/Vis spectroscopy. Conclusions on the ion pair structures of the alkali metal salts 9a ‐ e and 10a – c are drawn from the spectroscopic data. Additionally, in one case the behavior of the alkali metal salt 10b towards oxidants was studied by cyclic voltammetry and the structure of the corresponding hydrocarbon 8b was proved by X‐ray structural analysis.