Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts

Marie Betou 1 Raphael J. Durand 1 Antoine Sallustrau 1 Claire Gousset 1 Erwann Le Coz 1 Yann R. Leroux 1 Loic Toupet 2 Elzbieta Trzop 2 Thierry Roisnel 1 Yann Trolez 1
1 ISCR - Institut des Sciences Chimiques de Rennes
2 IPR - Institut de Physique de Rennes
Abstract : 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.
Keywords : Cycloaddition retro reactions optoelectronics dienes ynamides
Document type :
Journal articles
Complete list of metadatas

Cited literature [17 references]  Display  Hide  Download
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01544243
Contributor : Laurent Jonchère <>
Submitted on : Wednesday, July 5, 2017 - 4:26:58 PM
Last modification on : Saturday, December 22, 2018 - 7:33:31 PM
Long-term archiving on : Tuesday, January 23, 2018 - 9:58:03 PM

Files

Betou et al. - 2017 - Reactivi...
Files produced by the author(s)

Identifiers

Collections

UNIV-RENNES1 | SCR-CD | IPR | ISCR | ISCR-PRATS | IPR-ML | INC-CNRS | UR1-UFR-SPM | ISCR-CORINT | OSUR | UNIV-RENNES | INSA-RENNES | INSA-GROUPE

Citation

Marie Betou, Raphael J. Durand, Antoine Sallustrau, Claire Gousset, Erwann Le Coz, et al.. Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts. Chemistry - An Asian Journal, Wiley-VCH Verlag, 2017, 12 (12), pp.1338-1346. ⟨10.1002/asia.201700353⟩. ⟨hal-01544243⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

295

Files downloads

87