Effenberger, FranzBäuerle, PeterSeufert, WalterStohrer, Wolf-Dieter2009-08-272016-03-312009-08-272016-03-311990312053738http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-43688http://elib.uni-stuttgart.de/handle/11682/1138http://dx.doi.org/10.18419/opus-1121Iodo, bromo, chloro, and thiocyanato σ-complexes 4, accessible as crystalline compounds from 1,3,5-tris(1-pyrrolidinyl)benzene (1) with halogens and dirhodan, respectively, react with nucleophiles or bases under dehalogenation, deprotonation, dimerization, or H σ-complex formation. The product formation depends on the redox potentials of the σ-complexes (acceptors) and the nucleophiles (donors), on the leaving tendency of the substituents on C-1 of the σ-complexes, and on the reaction time. The unexpected reactions are interpreted by an electron transfer from the nucleophile Y| to the σ-complex A+ to give the radical A*, a subsequent heterolytic dissociation to the 1,3,5-tris(1-pyrrolidinyl)benzene radical cation C.+, and its follow-up reactions (addition of nucleophiles, dimerization, and H abstraction). The H σ-complex 6 results the most stable final product after long reaction times because of its lowest acceptor properties and the poor nucleofugal leaving tendency of a hydride ion.deinfo:eu-repo/semantics/openAccessTriaminobenzole , Elektronentransfer540article