Synthesis 2005(9): 1496-1506  
DOI: 10.1055/s-2005-869894
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Synthesis and Evaluation of New α-Hydrogen Nitroxides for ‘Living’ Free Radical Polymerization

Rebecca Braslau*, Greg O’Bryan, Aaron Nilsen, Jeff Henise, Thanchanok Thongpaisanwong, Erin Murphy, Laura Mueller, Jean Ruehl
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA
Fax: +1(831)4592935; e-Mail: braslau@chemistry.ucsc.edu;
Further Information

Publication History

Received 8 February 2005
Publication Date:
11 May 2005 (online)

Abstract

Three N-alkoxyamines were synthesized for use in nitroxide-mediated radical polymerization. Upon thermolysis, they generate new acyclic α-hydrogen nitroxides: one adamantyl substituted and two diol-containing nitroxides. The initiators were tested in polymerization reactions in direct comparison with the initiator derived from the nitroxide TIPNO.

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Use of THP as the hydroxy protecting group gives a more robust set of intermediates: Braslau, R.; Gonzalez, C., unpublished results from this laboratory.

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Braslau, R; Nilsen, A.; detailed studies on the decomposition of TIPNO will be reported in the near future.