Publication: Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers
Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers
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Schnell, S. D., Schilling, M., Sklyaruk, J., Linden, A., Luber, S., & Gademann, K. (2021). Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers. Organic Letters, 23(7), 2426–2430. https://doi.org/10.1021/acs.orglett.0c04113
Abstract
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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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- Schnell, Simon D
- Schilling, Mauro
- Sklyaruk, Jan
- Luber, Sandra
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Schnell, S. D., Schilling, M., Sklyaruk, J., Linden, A., Luber, S., & Gademann, K. (2021). Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers. Organic Letters, 23(7), 2426–2430. https://doi.org/10.1021/acs.orglett.0c04113
