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      Michael addition with an olefinic pyridine: organometallic nucleophiles and carbon electrophiles.

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      The Journal of organic chemistry

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          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.

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          Author and article information

          Journal
          2985193R
          5098
          J Org Chem
          J Org Chem
          The Journal of organic chemistry
          0022-3263
          1520-6904
          20 November 2020
          15 September 2020
          02 October 2020
          04 January 2021
          : 85
          : 19
          : 12740-12746
          Affiliations
          Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115
          Author notes
          Author information
          http://orcid.org/0000-0001-5271-699X
          Article
          PMC7781395 PMC7781395 7781395 nihpa1647789
          10.1021/acs.joc.0c00823
          7781395
          32883082
          38d8bd1b-38ae-4bcf-ad35-cf07eb03be3c
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