Tetrazinodihetarene: Synthese und Eigenschaften neuer mehrstufiger Redoxsysteme vom „Weitz‐Typ”︁

Abstract

Tetrazinodihetarenes: Synthesis and Properties of New Multistep “Weitz‐Type” Redox SystemsThe s‐tetrazine derivatives 3a–d and 6 were obtained by electrophilic amination of N‐heterocycles bearing a leaving group in α‐position and subsequent condensation under basic conditions. The corresponding N‐amino salts 2a–f, 5 and 7 could be isolated and characterised. Under the same conditions, it was not possible to obtain a corresponding tetrazine from 5 but the mesoionic hetarylium‐N‐imide 6 could be isolated. The structure of 11 was supported by X‐ray structure determination of its hydrogen sulfate salt. The redox potentials of the new compounds were determined by cyclovoltammetric methods. The tetrazines easily form radical salts which show unusually high stability.