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Can the First Addition of Alkyl Radicals Play a Role in the Fate of NMP?

✍ Scribed by Elena Bagryanskaya; Denis Bertin; Didier Gigmes; Igor Kirilyuk; Sylvain R. A. Marque; Vladimir Reznikov; Galina Roshchupkina; Irina Zhurko; Dmitry Zubenko

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
273 KB
Volume
209
Category
Article
ISSN
1022-1352

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Values of k~d~ for the Cο£ΏON bond homolysis were measured for alkoxyamines based on imidazoline and imidazole nitroxides. They were analyzed in terms of polar/stabilization, steric, and entropic effects. k~d~ decreased with increasing electron‐withdrawing capacities of the groups attached to the nitroxide, but increasing with both the bulkiness of the group attached to the nitroxide and the presence of substituents on the ring. With three alkoxyamines, it was shown that the fate of the NMP of styrene depended on the type of initiating alkyl radical: successful for initiating 1‐phenylethyl radicals and unsuccessful for initiating p‐nitrophenyloxycarbonyl‐2‐prop‐2‐yl radicals.

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