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Elucidation of the Alternating Copolymerization Mechanism of Epoxides or Aziridines with Cyclic Anhydrides in the Presence of Halide Salts by Jiaxi Xu; Pengfei Zhang; Youyou Yuan; Nikos Hadjichristidis is a Chemistry article available to read on EtoBox.

What is Elucidation of the Alternating Copolymerization Mechanism of Epoxides or Aziridines with Cyclic Anhydrides in the Presence of Halide Salts about?

Organic halide salts in combination with metal or organic compound are the most common and essential catalysts in ring-opening copolymerizations (ROCOP). However, the role of organic halide salts was neglected. Here, we have uncovered the complex behavior of organic halides in ROCOP of epoxides or aziridine with cyclic anhydride. Coordination of the chain-ends to cations, electron-withdrawing effect, leaving ability of halide atoms, chain-end basicity/nucleophilicity, and terminal steric hindrance cause three types of side reactions: single-site transesterification, substitution, and elimination. Understanding the complex functions of organic halide salts in ROCOP led us to develop highly active and selective aminocyclopropenium chlorides as catalysts/initiators. Adjustable Hbonding interactions of aminocyclopropenium with propagating anions and epoxides create chain-end coordination process that generate highly reactive carboxylate and highly selective alkoxide chain-ends.

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Author

Jiaxi Xu; Pengfei Zhang; Youyou Yuan; Nikos Hadjichristidis

Publisher

Wiley

Published

2023

Language

EN

Field

Chemistry (Physical Sciences)