88609-49-8Relevant academic research and scientific papers
Mechanism of the yeast mediated reduction of nitrostyrenes in light petroleum
McAnda, Anita F.,Roberts, Kade D.,Smallridge, Andrew J.,Ten, Abilio,Trewhella, Maurie A.
, p. 501 - 504 (2007/10/03)
The yeast mediated reduction of a range of α- and β-deutero substituted nitrostyrenes has been conducted in light petroleum in the presence of a small amount of water or D2O. NMR analysis of the products from these reactions has allowed the determination of the mechanism of this yeast reduction reaction. The results indicate that initially, a reversible non-stereoselective protonation occurs at the β-centre, followed by stereoselective addition of hydride at the α-position.
In Situ Generation and Synthetic Application of 2-Phenylbenzimidazoline to the Selective Reduction of Carbon-Carbon Double Bonds of Electron-Deficient Olefins
Chikashita, Hidenori,Nishida, Shuichi,Miyazaki, Makoto,Morita, Yasuhiro,Itoh, Kazuyoshi
, p. 737 - 746 (2007/10/02)
2-Phenylbenzimidazoline (PBI) as a mild, selective, and convenient reducing agent was efficiently generated in situ from o-phenylenediamine and benzaldehyde in alcohols.A generally applicable method for the selective reduction of carbon-carbon double bonds of a variety of electron-deficient olefins with an alcoholic solution of PBI is described.The reduction of α,β-unsaturated ketones to the corresponding saturated ketones could also be accomplished (but, less effectively) with PBI with the aid of a Lewis-acid catalyst. 1-Methyl-2-(o-nitrophenyl)benzimidazoline prepared and isolated by the reaction of o-nitrobenzaldehyde with N-methyl-o-phenylenediamine reduced benzylidenemalononitrile to give benzylmalononitrile and 1-methyl-2-(o-nitrophenyl)benzimidazoline in high yields.This shows the validity of PBI to be the actual reducing species in the present reduction system.From a mechanistic study, the present reductions could be interpreted in terms of a mechanism involving a synchronous transport of a pair of hydrogens or a sequential transfer of a hydride and a proton from PBI to the olefins.
