skip to main content
Idioma:

Post-Cycloaddition-Retroelectrocyclization Transformations of Polycyanobutadienes

Lacy, Adam R. ; Vogt, Anna ; Boudon, Corinne ; Gisselbrecht, Jean-Paul ; Schweizer, W. Bernd ; Diederich, François

European journal of organic chemistry, 2013-02, Vol.2013 (5), p.869-879 [Periódico revisado por pares]

Weinheim: WILEY-VCH Verlag

Texto completo disponível

Citações Citado por
  • Título:
    Post-Cycloaddition-Retroelectrocyclization Transformations of Polycyanobutadienes
  • Autor: Lacy, Adam R. ; Vogt, Anna ; Boudon, Corinne ; Gisselbrecht, Jean-Paul ; Schweizer, W. Bernd ; Diederich, François
  • Assuntos: Analytical chemistry ; Charge transfer ; Chromophores ; Cycloaddition ; Electrochemistry ; Electrocyclic reations ; Electron acceptors
  • É parte de: European journal of organic chemistry, 2013-02, Vol.2013 (5), p.869-879
  • Notas: ark:/67375/WNG-0J9NBGJL-M
    istex:E526C69CFE8EAC7FFAAE8DDA497B07B7B24F2B50
    ArticleID:EJOC201201371
  • Descrição: The thermal [2+2] cycloaddition–retroelectrocyclization (CA‐RE) reaction between a range of alkynes, activated by electron‐donating anilino (p‐H2NC6H4‐) substituents, and the electron‐deficient olefins tetracyanoethene (TCNE) and 7,7,8,8‐tetracyano‐p‐quinodimethane (TCNQ) delivered anilino‐substituted polycyanobutadienes (PCBDs). The aniline NH2 groups provide a convenient handle for further transformations, yielding a new series of PCBDs without an electron‐donating group. Electrochemical investigations by rotating disk voltammetry and cyclic voltammetry revealed large anodic shifts in both the first and second reduction potentials as a result of the removal of the electron‐donating functionality. This methodology allows for PCBD‐containing substrates to be further elaborated, generating a new family of chromophores previously inaccessible by alternative synthetic methods. The use of ethynylated anilines as activated alkynes in cycloaddition–retroelectrocyclization reactions with tetracyanoethene and tetracyanoquinodimethane provides access to novel, highly electron‐deficient polycyanobutadienes and unprecedented chromophores. Electrochemical studies show that the electron‐accepting abilities are strongly enhanced upon elimination of the amino donor substituent.
  • Editor: Weinheim: WILEY-VCH Verlag
  • Idioma: Inglês
Voltar para lista de resultados
Ir para página anteriorAnterior Resultado  6 AvançarIr para próxima página

  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

Buscando em bases de dados remotas. Favor aguardar.