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Chemically Triggered C-ON Bond Homolysis of Alkoxyamines. 8. Quaternization and Steric Effects

Abstract : The C-ON bond homolysis in alkoxyamine 2a was chemically triggered by quaternization of the 1-(pyridin-2-yl)ethyl fragment using protonation, acylation, and oxidation into the N-oxide. The solvent effect was also investigated, and DFT calculations were performed to explore this chemical activation. Alkoxyamines 2a-d were also compared to the 1-(pyridin-4-yl)ethyl analogues 3a-d.
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Submitted on : Monday, December 12, 2016 - 6:49:51 PM
Last modification on : Tuesday, December 14, 2021 - 8:42:06 AM

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Gérard Audran, Lionel Bosco, Paul Brémond, Sylvain R.A. Marque, Valérie Roubaud, et al.. Chemically Triggered C-ON Bond Homolysis of Alkoxyamines. 8. Quaternization and Steric Effects. Journal of Organic Chemistry, American Chemical Society, 2013, 78 (19), pp.9914--9920. ⟨10.1021/jo401674v⟩. ⟨hal-01415182⟩

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