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

Author:

Xu Jiaxi1ORCID,Zhang Pengfei1ORCID,Yuan Youyou2,Hadjichristidis Nikos1ORCID

Affiliation:

1. King Abdullah University of Science and Technology (KAUST) Physical Sciences and Engineering Division KAUST Catalysis Center Polymer Synthesis Laboratory Thuwal 23955 Saudi Arabia

2. King Abdullah University of Science and Technology (KAUST) Imaging and Characterization Core Lab Thuwal 23955 Saudi Arabia

Abstract

AbstractOrganic 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 H‐bonding interactions of aminocyclopropenium with propagating anions and epoxides create chain‐end coordination process that generate highly reactive carboxylate and highly selective alkoxide chain‐ends.

Publisher

Wiley

Subject

General Medicine

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