Orthoamides and Iminium Salts LXXVII.^{[ 1 ]} Cycloadditions to N,N,N′,N′,N′′,N′′,N′′′,N′′′-Octamethylacetylenedicarboxamidinium Bis(tetrafluoroborate): A New Synthetic Method for the Preparation of Heterocyclic Dicarboxamidinium Salts

Dedicated to Professor Dr. Volker Jäger on the occasion of his 70^th birthday

Abstract

The new, hitherto unknown, heterocyclic 1,2-dicarboxamidinium salts were prepared from N,N,N′,N′,N′′,N′′,N′′′,N′′′-octamethylacetylenedicarboxamidinium bis(tetrafluoroborate) and benzyl azide, C-phenyl-N-methylnitrone, (ethoxycarbonyl)pyridiniomethanide (prepared in situ from N-[(ethoxycarbonyl)methyl]pyridinium bromide), aromatic o-hydroxycarbaldehydes salicylaldehyde and 2-hydroxy-1-naphthaldehyde, 2-[(phenylimino)methyl]phenol, methyl salicylate, and phenyldiazomethane.

Key words

cycloaddition - azide - diazoalkane - nitrone - ylide - aromatic hydroxycarbaldehyde - hydroxy imine - aromatic 2-hydroxy esters - acetylenedicarboxamidinium bis(tetrafluoroborate) - heterocyclic bis(amidinium) salts

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