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Issue 9, 2014
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Synthesis and properties of long [n]cumulenes (n ≥ 5)

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Molecules composed of a contiguous sequence of double bonds, the [n]cumulenes, share structural similarities to both of their conjugated relatives, the polyenes and polyynes. The synthesis and properties of [n]cumulenes are, however, quite different from those of either polyenes or polyynes. At an infinite length, [n]cumulenes would provide one structural form of the hypothetical sp-hybridized carbon allotrope carbyne, while shorter derivatives offer model compounds to help to predict the properties of carbyne. Finally, derivatization of the π-electron framework of [n]cumulenes provides a number of different synthetic transformations, with cycloaddition reactions being the most common. In this review, both historical and recent synthetic achievements toward long [n]cumulenes (n ≥ 5) are discussed. This is followed by a description of our current understanding of the physical and electronic structure of [n]cumulenes based on UV/vis spectroscopy and X-ray crystallography. Finally, the reactivity of long [n]cumulenes is described.

Graphical abstract: Synthesis and properties of long [n]cumulenes (n ≥ 5)

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Publication details

The article was received on 15 Jan 2014 and first published on 27 Mar 2014

Article type: Review Article
DOI: 10.1039/C4CS00022F
Citation: Chem. Soc. Rev., 2014,43, 3184-3203
  • Open access: Creative Commons BY-NC license
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    Synthesis and properties of long [n]cumulenes (n ≥ 5)

    J. A. Januszewski and R. R. Tykwinski, Chem. Soc. Rev., 2014, 43, 3184
    DOI: 10.1039/C4CS00022F

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