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Tetrazinodihetarene: Synthese und Eigenschaften neuer mehrstufiger Redoxsysteme vom „Weitz‐Typ”︁
Author(s) -
Stumpf Martin,
Balli Heinz
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419941016
Subject(s) - chemistry , tetrazine , imide , mesoionic , amination , redox , polymer chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Tetrazinodihetarenes: Synthesis and Properties of New Multistep “Weitz‐Type” Redox Systems The 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.