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

Gérard Audran (1) , Lionel Bosco (1) , Paul Brémond (1) , Sylvain R.A. Marque (1) , Valérie Roubaud (1) , Didier Siri (1)

1 ICR - Institut de Chimie Radicalaire

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.

Domains: Theoretical and/or physical chemistry

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, 2013, 78 (19), pp.9914--9920. ⟨10.1021/jo401674v⟩. ⟨hal-01415182⟩