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Intramolecular Hydrogen Bond in Alkoxyamines. Influence on the C-ON Bond Homolysis

Abstract : The C-ON bond homolysis in alkoxyamines can be influenced by the presence of an intramolecular hydrogen bond (IHB) between the alkyl and the nitroxyl fragments, which leads to an 8-fold decrease in the homolysis rate constant k(d). When the IHB is disrupted by the solvent or by substitution of the hydrogen involved in the IHB by a protecting group (OMe, OAc, OBz, OBn, or OTBDMS), a higher homolysis rate constant k(d) is observed, as expected from the correlations developed by Marque (Bet-tin, D.; Gigmes, D.; Marque, S.; Tordo, P. Macromolecules 2005, 38, 2638-2650). Results were confirmed by DFT calculations at the B3LYP/6-31G(d,p) level.
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https://hal-amu.archives-ouvertes.fr/hal-01415180
Contributor : Didier Siri <>
Submitted on : Monday, December 12, 2016 - 6:49:47 PM
Last modification on : Thursday, January 18, 2018 - 2:30:58 AM

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Paul Brémond, Teddy Butscher, Valérie Roubaud, Didier Siri, Stéphane Viel. Intramolecular Hydrogen Bond in Alkoxyamines. Influence on the C-ON Bond Homolysis. Journal of Organic Chemistry, American Chemical Society, 2013, 78 (20), pp.10524--10529. ⟨10.1021/jo401681w⟩. ⟨hal-01415180⟩

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