A convenient synthesis of functionalized alkoxyamines as initiators for living free radical polymerization |
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| Authors: | Naoya Sugimoto Atsushi Narumi Toshifumi Satoh Harumi Kaga Toyoji Kakuchi |
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| Affiliation: | (1) Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan, JP;(2) National Institute of Advanced Industrial Science and Technology (AIST), 2-17-2- 1 Tsukisamu-Higashi, Toyohira, Sapporo 062-851 7, Japan, Tel (Fax) +8 1-1 1-706-6602. e-mail kakuchi@poly-mc.eng.hokudai.ac.jp, JP |
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| Abstract: | Summary 2,2,6,6-Tetramethylpiperidine- 1-oxyl (TEMPO) was reacted with ethylbenzene (la), 1-bromo-4-ethylbenzene (lb), and 4-ethylphenyl acetate (lc), respectively, using tert-BuOOWCo(OAc)·4H2O in acetonitrile at room temperature. The reactions produced the respective TEMPO-adducts (2a, 2b, and 2c) in the yields of 37, 44, and 45 %, which were based on TEMPO. Similarly, TEMPO was reacted with 4-ethylphenyl 2,3,6,2',3',4',6'-hepta-O-acetyl-β-D-cellobioside (1d) to afford the glycoconjugated TEMPO-adduct (2d) in 45 5% yield, which was based on 1d. These results indicated that the reaction has the potential to become an easy and also safe strategy, which provided various functionalized alkoxylamines. Received 20 November 2002/Revised Version: 5 December 2002/ Accepted: 7 December 2002 Correspondence to Naoya Sugimoto |
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