In Situ Generation and Synthetic Application of 2-Phenylbenzimidazoline to the Selective Reduction of Carbon–Carbon Double Bonds of Electron-Deficient Olefins

doi:10.1246/BCSJ.60.737

Paper

In Situ Generation and Synthetic Application of 2-Phenylbenzimidazoline to the Selective Reduction of Carbon–Carbon Double Bonds of Electron-Deficient Olefins

Published Feb 1, 1987 · H. Chikashita, Shuichi Nishida, M. Miyazaki

Bulletin of the Chemical Society of Japan

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72

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Abstract

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)benzimidazole 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...

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2-Phenylbenzimidazoline effectively reduces carbon-carbon double bonds in electron-deficient olefins, with potential applications in various industries.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

In Situ Generation and Synthetic Application of 2-Phenylbenzimidazoline to the Selective Reduction of Carbon–Carbon Double Bonds of Electron-Deficient Olefins

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References

AlCl3-Promoted Conjugate Reduction of α,β Unsaturated Carbonyl Compounds with 1,3-Dimethyl-2-phenylbenzimidazoline

AlCl3-promoted conjugate reduction of,-unsaturated carbonyl compounds with 1,3-dimethyl-2-phenylbenzimidazoline effectively converts them to saturated carbonyl compounds, with DMBI acting as a hydride-donating agent and Al

3-Methyl-2,3-dihydrobenzothiazoles as reducing agents. Dye enhanced photoreactions

N-alkyl-2,3-dihydrobenzothiazoles can reduce electron deficient saturated carbon atoms in visible light-initiated reactions, which can act as enolate carriers under electrophilic conditions.

An Efficient Method for the Selective Reduction of 2-Aryl-1-Nitroalkenes to 2-Aryl-1-Nitroalkanes by 2-Phenylbenzimidazoline

This study presents an efficient method for selective reduction of 2-aryl-1-nitroalkenes to 2-Aryl-1-Nitroalkanes using 2-phenylbenzimidazoline, resulting in high yields of useful compounds.

2-Phenylbenzimidazoline as a Reducing Agent in the Preparation of Malononitriles from α,β-Unsaturated Dinitriles

2-Phenylbenzimidazoline effectively reduces carbon-carbon double bonds in,-unsaturated dinitriles, providing a new synthetic method for selective reduction of strong electron-withdrawing groups.

Reduction of nitroalkenes to nitroalkanes with aqueous sodium borohydride

This method allows for efficient reduction of nitroalkenes to nitroalkanes, offering a new method for extending carbon chains and preparing nitroalkanes from aldehydes.

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