Literature DB >> 15932234

Superacid-catalyzed reactions of olefinic pyrazines: an example of anti-Markovnikov addition involving superelectrophiles.

Yiliang Zhang1, Jason Briski, Yun Zhang, Rendy Rendy, Douglas A Klumpp.   

Abstract

[reaction: see text] Olefinic pyrazines are found to react with benzene in CF3SO3H and give anti-Markovnikov-type addition products. We propose that this is caused by two effects: destabilization of the carbocationic intermediates that would lead to Markovnikov-type products and the generation of a considerable amount of positive charge at the terminal carbon of the olefinic groups. This suggests that acid-catalyzed addition reactions can give anti-Markovnikov-type products when a multiply charged (i.e., superelectrophilic) group is adjacent to the olefinic site.

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Year:  2005        PMID： 15932234      PMCID： PMC2883295          DOI： 10.1021/ol050900q

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Superacidic activation of 1- and 3-isoquinolinols and their electrophilic reactions.

Authors:  Konstantin Yu Koltunov; G K Surya Prakash; Golam Rasul; George A Olah
Journal:  J Org Chem       Date:  2002-12-13       Impact factor: 4.354

2.  Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: recent developments and trends.

Authors:  Matthias Beller; Jayasree Seayad; Annegret Tillack; Haijun Jiao
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-28       Impact factor: 15.336

3.  Superelectrophilic solvation.

Authors:  George A Olah; Douglas A Klumpp
Journal:  Acc Chem Res       Date:  2004-04       Impact factor: 22.384

4.  Optical and redox properties of a series of 3,4-ethylenedioxythiophene oligomers.

Authors:  Joke J Apperloo; L Bert Groenendaal; Hilde Verheyen; Manickam Jayakannan; René A J Janssen; Ahmed Dkhissi; David Beljonne; Roberto Lazzaroni; Jean-Luc Brédas
Journal:  Chemistry       Date:  2002-05-17       Impact factor: 5.236

5.  Dicationic electrophiles from olefinic amines in superacid.

Authors:  Yun Zhang; Aaron McElrea; Gregorio V Sanchez; Dat Do; Alma Gomez; Sharon L Aguirre; Rendy Rendy; Douglas A Klumpp
Journal:  J Org Chem       Date:  2003-06-27       Impact factor: 4.354

6.  Dicationic intermediates involving protonated amides: dual modes of reactivity including the acylation of arenes.

Authors:  Douglas A Klumpp; Rendy Rendy; Yun Zhang; Alma Gomez; Aaron McElrea
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005

7.  Superacid-catalyzed reactions of cinnamic acids and the role of superelectrophiles.

Authors:  Rendy Rendy; Yun Zhang; Aaron McElrea; Alma Gomez; Douglas A Klumpp
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354
  7 in total
  4 in total

1.  Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: mechanisms correlated to charge distributions.

Authors:  Yiliang Zhang; Matthew R Sheets; Erum K Raja; Kenneth N Boblak; Douglas A Klumpp
Journal:  J Am Chem Soc       Date:  2011-05-12       Impact factor: 15.419

2.  Friedel-Crafts acylation with amides.

Authors:  Erum K Raja; Daniel J DeSchepper; Sten O Nilsson Lill; Douglas A Klumpp
Journal:  J Org Chem       Date:  2012-06-21       Impact factor: 4.354

Review 3.  Superelectrophiles: Recent Advances.

Authors:  Douglas A Klumpp; Maksim V Anokhin
Journal:  Molecules       Date:  2020-07-19       Impact factor: 4.411

4.  Markovnikov-Type Hydrotrifluoromethylchalcogenation of Unactivated Terminal Alkenes with [Me4N][XCF3] (X = S, Se) and TfOH.

Authors:  Jin Shi; Cheng-Pan Zhang
Journal:  Molecules       Date:  2020-10-03       Impact factor: 4.411
  4 in total

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