1645293-05-5Relevant academic research and scientific papers
Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts
Betou, Marie,Durand, Rapha?l J.,Sallustrau, Dr Antoine,Gousset, Claire,Le Coz, Erwann,Leroux, Yann R.,Toupet, Dr Lo?c,Trzop, Elzbieta,Roisnel, Thierry,Trolez, Yann
, p. 1338 - 1346 (2017/06/23)
The reactivity of functionalized ynamides and arylynamines with tetracyanoethylene at room temperature was evaluated. In most cases, the corresponding 1,1,4,4-tetracyanobutadienes (TCBDs) were obtained in good to excellent yields through a [2+2]-cycloaddition/[2+2]-retro-electrocyclization sequence. The influence of diverse functional groups on the yield of the reaction was investigated, in particular concerning multiple ynamides. These TCBDs were characterized by various spectroscopic techniques and electrochemistry and X-ray diffraction in some cases.
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).
