Diels-Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5-Hexatriynes

Beitrag in einer Fachzeitschrift


Details zur Publikation

Autorinnen und Autoren: Sale AC, Murray AH, Prenzel D, Hampel F, De Luca L, Tykwinski R
Zeitschrift: European Journal of Organic Chemistry
Jahr der Veröffentlichung: 2016
Band: 2016
Heftnummer: 13
Seitenbereich: 2274-2283
ISSN: 1434-193X


Abstract

Diels--Alder cycloaddition reactions of 1,3,5-hexatriynes with tetraphenylcyclopentadienone have been performed, and mainly gave 1,2-diethynyl-3,4,5,6-tetraphenylbenzene derivatives as products. The Diels--Alder reactions were optimized under conventional heating and microwave irradiation conditions, and showed good selectivity towards the central carbon--carbon triple bond of the triyne. Empirical evidence suggests that the selectivity of the reaction is governed predominantly by the steric demands of the end-groups of the triyne. Several of the Diels--Alder products could be further elaborated by a sequence of desilylation and oxidative homocoupling to provide dimeric products. The homocoupling reaction was optimized by Pd catalysis. The X-ray crystallographic analysis of two derivatives is reported.


FAU-Autorinnen und Autoren / FAU-Herausgeberinnen und Herausgeber

Hampel, Frank Dr.
Lehrstuhl für Organische Chemie I
Prenzel, Dominik
Sonderforschungsbereich 953/2 Synthetische Kohlenstoffallotrope
Sale, Anna Chiara
Lehrstuhl für Organische Chemie I
Tykwinski, Rik Prof.
Lehrstuhl für Organische Chemie I


Zusätzliche Organisationseinheit(en)
Exzellenz-Cluster Engineering of Advanced Materials


Einrichtungen weiterer Autorinnen und Autoren

Università degli Studi di Sassari (UNISS)


Forschungsbereiche

B Nanoelectronic Materials
Exzellenz-Cluster Engineering of Advanced Materials


Zitierweisen

APA:
Sale, A.C., Murray, A.H., Prenzel, D., Hampel, F., De Luca, L., & Tykwinski, R. (2016). Diels-Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5-Hexatriynes. European Journal of Organic Chemistry, 2016(13), 2274-2283. https://dx.doi.org/10.1002/ejoc.201600116

MLA:
Sale, Anna Chiara, et al. "Diels-Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5-Hexatriynes." European Journal of Organic Chemistry 2016.13 (2016): 2274-2283.

BibTeX: 

Zuletzt aktualisiert 2019-18-03 um 12:23