Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers.

Autor:	Schnell SD; Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland., Schilling M; Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland., Sklyaruk J; Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland., Linden A; Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland., Luber S; Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland., Gademann K; Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2021 Apr 02; Vol. 23 (7), pp. 2426-2430. Date of Electronic Publication: 2021 Mar 11.
DOI:	10.1021/acs.orglett.0c04113
Abstrakt:	The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF 3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels-Alder reactions was evaluated theoretically and corroborated by experiments. The substrate dependency of this unusual reaction was rationalized by determination of the activation barriers and on the basis of the activation strain model by employing density functional theory.
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu