1645293-03-3Relevant academic research and scientific papers
High-yield formation of substituted tetracyanobutadienes from reaction of ynamides with tetracyanoethylene
Betou, Marie,Kerisit, Nicolas,Meledje, Esme,Leroux, Yann R.,Katan, Claudine,Halet, Jean-Francois,Guillemin, Jean-Claude,Trolez, Yann
supporting information, p. 9553 - 9557 (2014/08/18)
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. 2+2=Tetracyanobutadienes: The reaction between ynamides and tetracyanoethylene at room temperature in dichloromethane provides tetracyanobutadienes in good to quantitative yields, following a sequence of [2+2] cycloaddition-retroelectrocyclization (see scheme; EWG=electron- withdrawing group).
