Radical-polar crossover reactions with a water-soluble tetrathiafulvalene derivative

Organic Electron Donors as Powerful Single‐Electron Reducing Agents in Organic Synthesis

“…This particular pathway was attributed to the great reactivity of the nitrogen lone pair of electrons. [39] To afford an environmentally acceptable approach that avoids the use of toxic and troublesome reductants, such as tin reagents, both water-soluble [41] and polymer-supported [42] versions of TTF were prepared to facilitate the purification process. After basic regeneration, the polymer was re-used in two further cycles with a minimal decrease in activity.…”

Stable π-dimer of a tetrathiafulvalene cation radical encapsulated in the cavity of cucurbit[8]uril

“…1 ‡ No signal for the TTF moiety is observed in the 1 H NMR spectrum of 1 in D 2 O taken in air, which is presumably due to the presence of a small amount of the TTF radical cation (1 + ·) generated by air oxidation; a similar behavior has been reported before. 12 It also indicates that the radical cation of 1 is generated by air oxidation, but the equilibrium is in favor of the neutral species in the absence of CB [8]. However, in the presence of CB[8], the facile formation of the stable p-dimer of 1 + · inside CB[8] shifts the equilibrium toward the radical cation species.…”

Organische Elektronendonoren als leistungsfähige Ein‐Elektronen‐Reduktionsmittel in der organischen Synthese

“…Um herauszufinden, ob der konkurrierende Abfang von TTFC + vermieden werden kann, wurden verschiedene TTFähnliche Donoren getestet, darunter Dithiadiazafulvalene (DTDAFs) (Tabelle 1). [39] [39] Um einen umweltschonenden Ansatz zu realisieren, der die Verwendung von toxischen Reduktionsmitteln wie Zinnreagentien vermeidet, wurden wasserlçsliche [41] sowie auch polymergestützte [42] TTF-Varianten hergestellt, die einen leichteren Reinigungsprozess ermçglichen. Das Polymer konnte regeneriert und in zwei weiteren Reaktionszyklen wiederverwendet werden, wobei nur eine minimale Verringerung der Aktivität zu verzeichnen war.…”