High-Yield Formation of Substituted Tetracyanobutadienes from Reaction of Ynamides with Tetracyanoethylene.

Marie Betou (1) , Nicolas Kerisit (1) , Esme Meledje (1) , Yann R Leroux (1) , Claudine Katan (1) , Jean-François Halet (1) , Jean-Claude Guillemin (1) , Yann Trolez (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

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.

Mots clés: [2+2] cycloaddition; tetracyanobutadienes; tetracyanoethylene; ynamides

Domaines: Chimie organique

Marie Betou, Nicolas Kerisit, Esme Meledje, Yann R Leroux, Claudine Katan, et al.. High-Yield Formation of Substituted Tetracyanobutadienes from Reaction of Ynamides with Tetracyanoethylene.. Chemistry - A European Journal, 2014, 20 (31), pp.9553-9557. ⟨10.1002/chem.201402653⟩. ⟨hal-01017020⟩