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Ring opening polymerization of lactides and lactones by multimetallic alkyl zinc complexes derived from the acids Ph₂C(X)CO₂2H (X = OH, NH₂ )

Al-Khafaji, Yahya F.; Elsegood, Mark R. J.; Frese, Josef W. A.; Elsegood, Mark R.J.; Frese, Josef W.A.; Al-Khafaji, Yahya; Redshaw, Carl; Elsegood, Mark; Frese, Josef

Authors

Yahya F. Al-Khafaji

Mark R. J. Elsegood

Josef W. A. Frese

Mark R.J. Elsegood

Josef W.A. Frese

Yahya Al-Khafaji

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Mark Elsegood

Josef Frese



Abstract

The reaction of the dialkylzinc reagents R₂Zn with the acids 2,2-Ph₂C(X)(CO₂H), where X = NH₂, OH, i.e. 2,2′-diphenylglycine (dpgH) or benzilic acid (benzH2), in toluene at reflux temperature afforded the tetra-nuclear ring complexes [RZn(dpg)]₄, where R = Me (1), Et (2), 2-CF₃C₆H₄ (3), and 2,4,6-F₃C₆H₂ (4); complex 2 has been previously reported. The crystal structures of 1·(2MeCN), 3 and 4·(4(C₇H₈)·1.59(H₂O)) are reported, along with that of the intermediate compound (2-CF₃C₆H₄)3B·MeCN and the known compound [ZnCl₂(NCMe)₂]. Complexes 1–4, together with the known complex [(ZnEt)₃(ZnL)₃(benz)₃] (5; L = MeCN), have been screened, in the absence of benzyl alcohol, for their potential to act as catalysts for the ring opening polymerization (ROP) of ε-caprolactone (ε-CL), δ-valerolactone (δ-VL) and rac-lactide (rac-LA); the co-polymerization of ε-CL with rac-LA was also studied. Complexes 3 and 4 bearing fluorinated aryls at zinc were found to afford the highest activities.

Journal Article Type Article
Publication Date Jan 1, 2017
Journal RSC advances
Print ISSN 2046-2069
Electronic ISSN 2046-2069
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 7
Issue 8
Pages 4510-4517
Institution Citation Al-Khafaji, Y. F., Elsegood, M. R. J., Frese, J. W. A., Elsegood, M. R., Frese, J. W., Al-Khafaji, Y., …Frese, J. (2017). Ring opening polymerization of lactides and lactones by multimetallic alkyl zinc complexes derived from the acids Ph₂C(X)CO₂2H (X = OH, NH₂ ). RSC advances, 7(8), 4510-4517. https://doi.org/10.1039/C6RA26746G
DOI https://doi.org/10.1039/C6RA26746G
Keywords Polymerization, Lactides, Lactones
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2017/RA/C6RA26746G#!divAbstract
Additional Information : This document is Similarity Check deposited; : Supplementary Information; : Crystal Structure Data; : Mark R. J. Elsegood (ORCID); : Carl Redshaw (ORCID); : The Royal Society of Chemistry has an exclusive publication licence for this journal; OPEN ACCESS: This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0); : Single-blind; : Received 13 November 2016; Accepted 19 December 2016; Version of Record published 16 January 2017

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