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Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers


Schnell, Simon D; Schilling, Mauro; Sklyaruk, Jan; Linden, Anthony; Luber, Sandra; Gademann, Karl (2021). Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers. Organic Letters, 23(7):2426-2430.

Abstract

The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels–Alder reactions was evaluat-ed 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.

Abstract

The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels–Alder reactions was evaluat-ed 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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry, Physical and Theoretical Chemistry, Biochemistry
Language:English
Date:2 April 2021
Deposited On:17 Jan 2022 16:21
Last Modified:27 Mar 2024 03:06
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.orglett.0c04113
  • Content: Accepted Version
  • Language: English