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Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts
Author(s) -
Betou Marie,
Durand Raphaël J.,
Sallustrau Dr Antoine,
Gousset Claire,
Le Coz Erwann,
Leroux Yann R.,
Toupet Dr Loïc,
Trzop Elzbieta,
Roisnel Thierry,
Trolez Yann
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700353
Subject(s) - tetracyanoethylene , cycloaddition , reactivity (psychology) , adduct , electrochemistry , scope (computer science) , yield (engineering) , chemistry , diffraction , photochemistry , combinatorial chemistry , materials science , organic chemistry , computer science , optics , physics , catalysis , programming language , composite material , medicine , alternative medicine , pathology , electrode
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.