Structural and Electronic Effects of Stepwise Reduction of a Tetraaryl[3]Cumulene

Beitrag in einer Fachzeitschrift


Details zur Publikation

Autorinnen und Autoren: Spisak SN, Bühringer M, Wei Z, Zhou Z, Tykwinski R, Petrukhina MA
Zeitschrift: Angewandte Chemie-International Edition
Jahr der Veröffentlichung: 2019
Band: 58
Heftnummer: 7
Seitenbereich: 2023-2028
ISSN: 1433-7851


Abstract

The chemical reduction of a [3]cumulene ([3]TrTol) has been explored using alkali metals. Mono- and doubly reduced forms of [3]TrTol were isolated as solvent-separated ion pairs with {Na(18-crown-6)THF2}(+) and {K(18-crown-6)THF2}(+) counterions and crystallographically characterized. This allowed analysis of structural parameters of the naked anions of [3]TrTol without interference from metal binding. The dianion of [3]TrTol was also isolated as a contact-ion complex with {Cs(18-crown-6)}(+) cations, thereby adding the effect of metal coordination to the core. Structural comparisons of anions to the neutral molecule, [3]TrTol, outline monotonic increases in bond-length alternation (BLA) upon stepwise reduction. The greatest BLA value is found for the contact-ion complex, which shows an alternating sequence of short and long carbon-carbon bonds, consistent with the structure of an alkyne. In contrast to studies on tetraphenyl[3]cumulene, the cumulenic framework of [3]TrTol remains planar in all the derivatives.


FAU-Autorinnen und Autoren / FAU-Herausgeberinnen und Herausgeber

Bühringer, Martina
Lehrstuhl für Organische Chemie I
Tykwinski, Rik Prof.
Lehrstuhl für Organische Chemie I


Einrichtungen weiterer Autorinnen und Autoren

State University of New York (SUNY) Stony Brook


Zitierweisen

APA:
Spisak, S.N., Bühringer, M., Wei, Z., Zhou, Z., Tykwinski, R., & Petrukhina, M.A. (2019). Structural and Electronic Effects of Stepwise Reduction of a Tetraaryl[3]Cumulene. Angewandte Chemie-International Edition, 58(7), 2023-2028. https://dx.doi.org/10.1002/anie.201812283

MLA:
Spisak, Sarah N., et al. "Structural and Electronic Effects of Stepwise Reduction of a Tetraaryl[3]Cumulene." Angewandte Chemie-International Edition 58.7 (2019): 2023-2028.

BibTeX: 

Zuletzt aktualisiert 2019-05-03 um 00:08