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Synfacts 2007(12): 1264-1264  
DOI: 10.1055/s-2007-991354
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

New Class of Chromophores via Cascade Reactions

Contributor(s): Timothy M. Swager, Jeewoo Lim
M. Kivala, C. Boudon, J.-P. Gisselbrecht, P. Seiler, M. Gross, F. Diederich*
ETH Zürich, Switzerland and Université Louis Pasteur, Strasbourg, France
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Publication History

Publication Date:
22 November 2007 (online)

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Significance

The authors report a synthesis of a variety of interesting materials using tandem thermal [2+2]-cycloaddition-retro-electrocyclization reactions. The reaction is high-yielding, atom-economical, and selective; electron-poor tetracyanoethylene (TCNE) and the electron-rich tetrathia­fulvalene (TTF) show selectivities for electron-rich and electron-poor alkynes, respectively.