C-ON bond homolysis in alkoxyamines. Part 12: the effect of the para-substituent in the 1-phenylethyl fragment - Archive ouverte HAL Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2016

C-ON bond homolysis in alkoxyamines. Part 12: the effect of the para-substituent in the 1-phenylethyl fragment

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Abstract

The application of alkoxyamines as initiators/controllers in nitroxide mediated polymerization and as agents for theranostics requires the development of switchable (from stable one to labile one) alkoxyamines. One way to achieve this is to tune the polarity of various groups carried by either the alkyl fragment or the nitroxyl fragment. Thus, the effect of protonation/deprotonation of the para-functionalized aryl moiety carried by the alkyl fragment in diethyl(2,2-dimethyl-1-((1,1-dimethylethyl)(1-para-subsituted-phenylethoxy) amino) propyl) phosphonate is investigated. An increase in k(d) is observed with increasing localized electrical effect, i.e., in the presence of electron withdrawing groups at the para position of the phenyl ring. A striking effect of the intimate ion pair on kd is also observed.
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Dates and versions

hal-01408206 , version 1 (03-12-2016)

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Gérard Audran, Paul Brémond, Jean-Patrick Joly, Marque S.R.A., Toshihide Yamasaki. C-ON bond homolysis in alkoxyamines. Part 12: the effect of the para-substituent in the 1-phenylethyl fragment. Organic & Biomolecular Chemistry, 2016, 14 (14), pp.3574-3583. ⟨10.1039/c6ob00384b⟩. ⟨hal-01408206⟩
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