Orthoamides and Iminium Salts LXXII: N,N,N′,N′,N′′,N′′,N′′′,N′′′-Octamethyl-(but-2-yne)-bis(amidinium) Tetrafluoroborate: The First Bis-amidinium Salt of Acetylenedicarboxyclic Acid. A New Superelectrophile?

A method for the preparation of the first acetylenedicarboxamidinium salt from a bis‐orthoamide derivative of acetylenedicarboxyclic acid has been established. The salt reacted with cyclopentadiene and furan at room temperature to give bicyclic [4+2]‐cycloaddition products. The solid compounds were...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-06, Vol.18 (23), p.7224-7228
Main Authors: Drandarov, Konstantin, Tiritiris, Ioannis, Wassiljew, Olga, Siehl, Hans-Ullrich, Kantlehner, Willi
Format: Article
Language:English
Subjects:
bis-orthoamides
Chemistry
Crystals
cycloaddition
Diffraction
NMR spectroscopy
quantum chemical calculations
X-ray diffraction
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Summary:A method for the preparation of the first acetylenedicarboxamidinium salt from a bis‐orthoamide derivative of acetylenedicarboxyclic acid has been established. The salt reacted with cyclopentadiene and furan at room temperature to give bicyclic [4+2]‐cycloaddition products. The solid compounds were characterized by solution NMR spectroscopy and by single‐crystal X‐ray diffraction. Quantum‐chemical calculations of the isolated N,N,N′,N′,N′′,N′′,N′′′,N′′′‐octamethyl‐acetylene‐bis(carboxamidinium) ion showed very good agreement with the spectroscopic and diffraction data. Highly charged, but superelectrophilic? The acetylene‐bis(carboxamidinium) salt, which was obtained from a bis‐orthoamide derivative of acetylenedicarboxyclic acid, reacted with cyclopentadiene and furan to give bicyclic [4+2]‐cycloaddition products (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201103695