3-Pyrrolidone, 1-butyl-, reduction

Fuchigami and coworkers have formed emlates with electrogenerated bases (equations 10 and 11). - The basic anions of 2,6-di-r-butyl-p-cresol and a-pyrrolidone were obtained by cathodic reduction. Countercations with a weak affinity for the fluorine atom e.g. quaternary ammonium, phosphonium or tertiary sulfonium cations) had to be used in the example shown in equation (11) in order to impede defluorination. 

Electrolytic reduction is also sometimes used. For instance, electrolysis of l-butyl-3-pyrrolidone in 30% sulfuric acid at 60° and at a cadmium cathode with a current density of 0.053-0.073 A/cm2 opens the ring, affording dibutyl-amine in 64% yield.543... 

Polymers provide metal NP stabilization not only because of the steric bulk of their framework, but also by weak binding to the NP surface by the heteroatom, playing the role of ligands. Poly(N-vinyl-2-pyrrolidone) (PVP) is the most commonly used polymer for NP stabilization and catalysis, because it fulfils both steric and ligand requirements [5f. For instance Pt-, Pd- and RhNPs stabilized by PVP, are synthesized by refluxing ethanolic reduction of the corresponding metal halide and immobilized in an ionic liquid, l-n-butyl-3-methylimidazolium hexafluorophos-phate ([BMI][PF 5]), and are very efficient olefin and benzene hydrogenation catalysts at 40 °C that can be recycled without loss of activity (see Chart 1.1 for the two major polymer formulas used for NP catalysis) [12k]. 

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