Electronic structure of 1,4-dihydro-1,2,4,5-tetrazines and of related 1,4-dihydroaromatic compounds

. Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1985)


1,4-Dihydro-1,2,4,5-tetrazine (I) and its 1,4-di-Me and 1,4-bis(trimethylsilyl) derivs. were studied by photoelectron spectroscopy and cyclic voltammetry. The compds. are electron-rich, albeit not as much as the corresponding 1,4-dihydropyrazines. Electrochem. data illustrate the stability of the 1,4-dihydro form in the tetrazine system and of the radical cation oxidn. state in the pyrazine system. Results of MNDO calcns. for I and for 1,4-dihydrobenzene, -pyrazine, and -hexazine indicate a contraction of bonds in the 6-membered ring upon consecutive replacement of CH by N, accompanied by increasing deviation from planarity and decreasing p electron conjugation. on SciFinder(R)

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