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A New Sterically Highly Hindered 7-Membered Cyclic Nitroxide for the Controlled Living Radical Polymerization

✍ Scribed by Che-Chien Chang; Kai Oliver Siegenthaler; Armido Studer

Book ID: 102253784
Publisher: John Wiley and Sons
Year: 2006
Tongue: German
Weight: 115 KB
Volume: 89
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200690206

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✦ Synopsis

Abstract

The synthesis of a new sterically highly hindered 7‐membered alkoxyamine, 2,2,7,7‐tetraethyl‐1‐(1‐phenylethoxy)‐1,4‐diazepan‐5‐one (4), starting from known 2,2,6,6‐tetraethyl‐1‐(1‐phenylethoxy)piperidin‐4‐one (3) via a Beckmann‐type rearrangement is presented. It is shown that ring‐enlargement by insertion of an NH moiety in going from 3 to 4 leads to a more efficient regulator for nitroxide‐mediated controlled living radical styrene (= ethenylbenzene) and butyl acrylate (= butyl prop‐2‐enoate) polymerization. In addition to the polymerization experiments, kinetic data on the reversible CO bond homolysis of alkoxyamines 3 and 4 are presented.

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