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Updated: Oct 13, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of
Marie Betou1, Raphaël J Durand1, Dr Antoine Sallustrau1
1Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS, Ecole Nationale Supérieure de Chimie de Rennes, Université de Rennes 1, 35708, Rennes Cedex, France.
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.
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