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The first crystal structure analysis of a 1,4-dihydroquinoxaline is described by example of the 1,4-bis(tert-butyldimethylsilyl) derivative. In the solid state, this molecule exhibits a nonplanar heterocycle with a dihedral angle of 156.3° along the N—N axis in the boat-shaped 8π electron ring system. The alkyl groups of the Si(tert-Bu)Me 2  substituents are arranged as to minimize steric repulsion. Despite the reduced π electron conjugation due to non-planarity, the compound is oxidized reversibly to an EPR detectable radical cation at —0.59 V vs. ferrocene in dichloromethane. However, the second oxidation to the fully aromatic dication is electrochemically irreversible. A comparison with previously obtained results illustrates the structural flexibility of the non-aromatic 1,4-dihydro-1,4-diazine ring system which is strongly affected by rather weak non-bonded interactions.

zeitschrift für naturforschung b

Erste strukturelle Charakterisierung eines leicht oxidierbaren 1,4-Dihydrochinoxalin-Derivats / First Structural Characterization of an Easily Oxidized Derivative of 1,4-Dihydroquinoxaline