Unexpected Formation of a [4]Radialene and Dendralenes by Addition of Tetracyanoethylene to a Tetraaryl[5]cumulene

Januszewski J, Hampel F, Neiß C, Görling A, Tykwinski R (2014)


Publication Language: English

Publication Status: Published

Publication Type: Journal article, Original article

Publication year: 2014

Journal

Publisher: Wiley-VCH Verlag

Book Volume: 53

Pages Range: 3743-3747

Journal Issue: 14

DOI: 10.1002/anie.201309355

Abstract

The use of cumulenes in synthetic transformations offers the possibility to form structurally interesting and potentially useful conjugated molecules. The cycloaddition reaction of a tetraaryl[5]cumulene with the electron-deficient olefin tetracyanoethylene affords unusual products, including functionalized dendralenes and alkylidene cyclobutanes, as well as a symmetric [4]radialene that shows unique solvato-chromism, with lambda(max) values approaching the near-IR region. These carbon-rich products have been investigated spectroscopically and by X-ray crystallographic analysis (five structures). The cycloaddition reaction sequence has also been explored by mechanistic and theoretical studies. The obtained results clearly demonstrate the potential of [5]cumulenes to serve as precursors for unprecedented conjugated structures.

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How to cite

APA:

Januszewski, J., Hampel, F., Neiß, C., Görling, A., & Tykwinski, R. (2014). Unexpected Formation of a [4]Radialene and Dendralenes by Addition of Tetracyanoethylene to a Tetraaryl[5]cumulene. Angewandte Chemie International Edition, 53(14), 3743-3747. https://dx.doi.org/10.1002/anie.201309355

MLA:

Januszewski, Johanna, et al. "Unexpected Formation of a [4]Radialene and Dendralenes by Addition of Tetracyanoethylene to a Tetraaryl[5]cumulene." Angewandte Chemie International Edition 53.14 (2014): 3743-3747.

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