Literature DB >> 24958540

High-yield formation of substituted tetracyanobutadienes from reaction of ynamides with tetracyanoethylene.

Marie Betou1, Nicolas Kerisit, Esme Meledje, Yann R Leroux, Claudine Katan, Jean-François Halet, Jean-Claude Guillemin, Yann Trolez.   

Abstract

A high-yielding sequence of [2+2] cycloaddition-retroelectrocyclization of ynamides with tetracyanoethylene (TCNE) is described. The reaction provided tetracyanobutadiene (TCBD) species, which were characterized by various techniques. DFT and TD-DFT calculations were also performed to complement experimental findings.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  [2+2] cycloaddition; tetracyanobutadienes; tetracyanoethylene; ynamides

Year:  2014        PMID: 24958540     DOI: 10.1002/chem.201402653

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  2 in total

1.  A Silver(I)-Catalyzed Intramolecular Ficini's [2 + 2] Cycloaddition Employing Ynamides.

Authors:  Xiao-Na Wang; Zhi-Xiong Ma; Jun Deng; Richard P Hsung
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes.

Authors:  Clotilde Philippe; Anh Thy Bui; Sabrinah Batsongo-Boulingui; Ziemowit Pokladek; Katarzyna Matczyszyn; Olivier Mongin; Loïc Lemiègre; Frédéric Paul; Trevor A Hamlin; Yann Trolez
Journal:  Org Lett       Date:  2021-02-26       Impact factor: 6.005

  2 in total

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