A New Sterically Highly Hindered 7‐Membered Cyclic Nitroxide for the Controlled Living Radical Polymerization | Zendy

Chang CheChien | Zendy; Siegenthaler Kai Oliver | Zendy; Studer Armido | Zendy

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

Author(s) -

Chang CheChien,

Siegenthaler Kai Oliver,

Studer Armido

Publication year - 2006

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200690206

Subject(s) - chemistry , nitroxide mediated radical polymerization , steric effects , homolysis , moiety , polymerization , radical polymerization , polymer chemistry , styrene , acrylate , radical , photochemistry , polymer , organic chemistry , copolymer

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 CO bond homolysis of alkoxyamines 3 and 4 are presented.

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