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Updated: Jul 11, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
Published on: November 21, 2017
Zinc anilido-oxazolinate complexes as initiators for ring opening polymerization
Chi-Tien Chen1, Chi-Yu Chan, Chi-An Huang
1Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan. ctchen@dragon.nchu.edu.tw
Abstract:
Three new anilido-oxazolines, ortho-C(6)H(4)(NHAr')(4,4-dimethyl-2-oxazoline) [Ar'=2,4,6-trimethylphenyl, HNPh(TriMe)Oxa (1); 2,6-diisopropylphenyl, HNPh(DiiPr)Oxa (2); 2-methoxyphenyl, HNPh(OMe)Oxa (3)], have been prepared. Reactions of 1 or 2 with one molar equivalent of ZnEt(2) in tetrahydrofuran or hexane solution give the zinc ethyl complexes (NPh(TriMe)Oxa)ZnEt (4) and (NPh(DiiPr)Oxa)ZnEt (5). The dinuclear zinc benzyloxide complexes, [(NAr'Oxa)Zn(mu-OBn)](2), [Ar'=2,4,6-trimethylphenyl, (6); 2-methoxyphenyl, (7)], were synthesized by the reaction of 4 with one molar equivalent of benzyl alcohol in tetrahydrofuran solution (for 6) or by treatment of with 3 one molar equivalent of ZnEt(2) in tetrahydrofuran solution followed by the addition of one molar equivalent of benzyl alcohol (for 7). The molecular structures are reported for compounds 6 and 7. Their catalytic activities toward the ring opening polymerization reactions are under investigation.
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Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

