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Chemically Triggered C-ON Bond Homolysis of Alkoxyamines. Quaternization of the Alkyl Fragment

Abstract : The C-ON bond homolysis in alkoxyamine 2a can be chemically triggered by the protonation of the 4-pyridylalkyl fragment. The resulting 15-fold increase In k(d) (Chem. Commun. 2011, 47, 4291-4293) was investigated experimentally and theoretically by quaternization of the pyridyl moiety using methylating (MeOTs), acylating (AcCl), and benzylating (PhCH2Br) agents as well as by oxidation of the pyridyl moiety into N-oxide and by the formation of a dative bond with BH3 as a Lewis acid.
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https://hal-amu.archives-ouvertes.fr/hal-01415186
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Submitted on : Monday, December 12, 2016 - 6:49:56 PM
Last modification on : Tuesday, October 13, 2020 - 3:10:13 AM

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Paul Brémond, Abdoulaye Koita, Sylvain R.A. Marque, Vincent Pesce, Valérie Roubaud, et al.. Chemically Triggered C-ON Bond Homolysis of Alkoxyamines. Quaternization of the Alkyl Fragment. Organic Letters, American Chemical Society, 2012, 14 (1), pp.358--361. ⟨10.1021/ol2031075⟩. ⟨hal-01415186⟩

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