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

Journal article
(Review article)

Publication Details

Author(s): Januszewski J, Tykwinski R
Journal: Chemical Society Reviews
Publisher: Royal Society of Chemistry
Publication year: 2014
Volume: 43
Journal issue: 9
Pages range: 3184-3203
ISSN: 0306-0012
eISSN: 1460-4744


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. This journal is © the Partner Organisations 2014.

FAU Authors / FAU Editors

Januszewski, Johanna Dr.
Tykwinski, Rik Prof.
Sonderforschungsbereich 953/2 Synthetische Kohlenstoffallotrope
Lehrstuhl für Organische Chemie I

Additional Organisation
Exzellenz-Cluster Engineering of Advanced Materials

Research Fields

B Nanoelectronic Materials
Exzellenz-Cluster Engineering of Advanced Materials

How to cite

Januszewski, J., & Tykwinski, R. (2014). Synthesis and properties of long [n]cumulenes (n ≥ 5). Chemical Society Reviews, 43(9), 3184-3203.

Januszewski, Johanna, and Rik Tykwinski. "Synthesis and properties of long [n]cumulenes (n ≥ 5)." Chemical Society Reviews 43.9 (2014): 3184-3203.


Last updated on 2019-07-04 at 14:50