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Michael Addition with an Olefinic Pyridine: Organometallic Nucleophiles and Carbon Electrophiles.

ABSTRACT: The conjugate addition reactions of trans-1,2-di(2-pyridyl)ethylene have been studied. This substrate reacts with organolithium nucleophiles, and the resulting anionic intermediates may be trapped by proton or various carbonyl-based electrophiles. It is suggested that the dipyridyl structure stabilizes the intermediate carbanion, allowing the Michael adduct to be captured by an added electrophile.

SUBMITTER: Stentzel MR 

PROVIDER: S-EPMC7781395 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Michael Addition with an Olefinic Pyridine: Organometallic Nucleophiles and Carbon Electrophiles.

Stentzel Michael R MR   Klumpp Douglas A DA  

The Journal of organic chemistry 20200915 19

The conjugate addition reactions of <i>trans</i>-1,2-di(2-pyridyl)ethylene have been studied. This substrate reacts with organolithium nucleophiles, and the resulting anionic intermediates may be trapped by proton or various carbonyl-based electrophiles. It is suggested that the dipyridyl structure stabilizes the intermediate carbanion, allowing the Michael adduct to be captured by an added electrophile. ...[more]

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