On the road to stable, isolable [4]cumulenes: Reactivity and cyclization reactions
Johnson MA, Meckes JA, Bühringer M, Zhou Z, Kuwatani Y, Ferguson MJ, Wei Z, Iyoda M, Petrukhina MA, Tykwinski RR (2022)
Publication Type: Journal article
Publication year: 2022
Journal
DOI: 10.1002/poc.4454
Abstract
The design and synthesis of persistent tetraaryl[4]cumulenes are reported. Derivatives with phenyl endgroups ([4]Ph and [4]Ph/Ar*) are susceptible to reactions during synthesis and/or purification that complicate isolation of the desired product, particularly intermolecular dimerization reactions. Incorporation of (3,5-di-tert-butyl)phenyl endgroups (Ar*) provides increased stability, culminating in the stable and isolable [4]cumulene [4]Ar*. Cumulene [4]Ar* remains, however, susceptible to dimerization under pressing conditions, and [4]Ar* also readily reacts with electrophiles under mild conditions that lead to intramolecular cyclization. Given the structural complexity of the side products in these studies (compounds 3, 10, 14, 17, 18), X-ray crystallography plays a vital role in their identification.
Authors with CRIS profile
Involved external institutions
University of Alberta
Canada (CA)
State University of New York at Albany (UNY Albany / UAlbany)
United States (USA) (US)
Tokyo Metropolitan University (TMU) / 首都大学東京
Japan (JP)
Canada (CA)
State University of New York at Albany (UNY Albany / UAlbany)
United States (USA) (US)
Tokyo Metropolitan University (TMU) / 首都大学東京
Japan (JP)
How to cite
APA:
Johnson, M.A., Meckes, J.A., Bühringer, M., Zhou, Z., Kuwatani, Y., Ferguson, M.J.,... Tykwinski, R.R. (2022). On the road to stable, isolable [4]cumulenes: Reactivity and cyclization reactions. Journal of Physical Organic Chemistry. https://doi.org/10.1002/poc.4454
MLA:
Johnson, Matthew A., et al. "On the road to stable, isolable [4]cumulenes: Reactivity and cyclization reactions." Journal of Physical Organic Chemistry (2022).
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