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Chem Commun (Camb). 2018 Dec 20;55(2):190-193. doi: 10.1039/c8cc08541b.

Versatile approach to activation of alkoxyamine homolysis by 1,3-dipolar cycloaddition for efficient and safe nitroxide mediated polymerization.

Chemical communications (Cambridge, England)

Mariya Edeleva, Denis Morozov, Dmitriy Parkhomenko, Yulia Polienko, Anna Iurchenkova, Igor Kirilyuk, Elena Bagryanskaya

Affiliations

  1. N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, 9 Pr. Lavrentjeva, Novosibirsk 630090, Russia.

PMID: 30519689 DOI: 10.1039/c8cc08541b

Abstract

An alkoxyamine was prepared from a cyclic aldonitrone nitroxide. The resulting alkoxyamine containing an aldonitrone functional substituent is relatively stable but can react readily with vinyl monomers to form a cycloadduct that has a much higher C-ON homolysis rate. This type of in situ activation converts the aldonitrone alkoxyamine into an efficient controlling agent for nitroxide-mediated polymerization. Here we present a study on this reaction of C-ON bond homolysis and application of such an alkoxyamine as an in situ-activated initiator.

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