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Magnesium and zinc complexes of a potentially tridentate β-diketiminate ligand
Abstract
The synthesis of the unsymmetrically substituted beta-diketimine, 2-(2-methoxyphenylimino)-4-(2,6-diisopropylphenylamido)pent-2-ene, (BDI-2)H, is described and its complexation chemistry with magnesium and zinc is explored. Emphasis is placed on the preparation of alkoxide and amide derivatives for the ring-opening polymerisation of lactide; their behaviour as polymerisation initiators is compared to analogous compounds supported by the N,N'-bis(2,6-diisopropylphenyl) beta-diketiminate ligand, BDI-1. (BDI-2)H reacts with Me2Mg to give the bis(chelate) complex, (BDI-2)2Mg, 3. Magnesium alkyls supported by BDI-2 may be prepared by increasing the size of the alkyl group. Hence, lithiation of (BDI-2)H affords [(BDI-2)Li]2, 4; its subsequent treatment with iPrMgCl produces (BDI-2)MgiPr, 5. Aminolysis of complex using iPr2NH yields the amide complex, (BDI-2)MgNiPr2, 6. Zn(NTMS2)2 and ZnEt2 react with (BDI-2)H to give (BDI-2)Zn(NTMS2), 7, and (BDI-2)ZnEt, 8, respectively. The former is converted into the siloxide complex, (BDI-2)Zn(OSiPh3), 9, upon reaction with Ph3SiOH. The chloride derivative, (BDI-2)ZnCl, 10, has also been prepared via the reaction of ZnCl2 with 4. Crystallographic analysis of compounds, and reveals that the potential for (BDI-2) to bind in a tridentate manner is only realised with the more electrophilic metals Li and Mg. Compared to their (BDI-1) counterparts, complexes 6, 7 and 9 are more active, but less well-controlled, initiators for the ring-opening polymerisation of rac-lactide, a consequence of the diminished steric protection afforded by (BDI-2) relative to (BDI-1).
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Citations
Cites
Polymerization of Lactide with Zinc and Magnesium β-Diiminate Complexes: Stereocontrol and Mechanism
Chamberlain, B. M., Cheng, M., Moore, D. R., Ovitt, T. M., Lobkovsky, E. B., & Coates, G. W. (2001) · Journal of the American Chemical Society · doi:10.1021/ja003851f · Cited by 1,207
Cited by
Biocompatible Initiators for Lactide Polymerization
Platel, R., Hodgson, L., & Williams, C. (2008) · Polymer Reviews · doi:10.1080/15583720701834166 · Cited by 706
Complexes of Mg, Ca and Zn as homogeneous catalysts for lactide polymerization
Wheaton, C. A., Hayes, P. G., & Ireland, B. J. (2009) · Dalton Transactions · doi:10.1039/b819107g · Cited by 438
Crimmin, M. R., Arrowsmith, M., Barrett, A. G. M., Casely, I. J., Hill, M. S., & Procopiou, P. A. (2009) · Journal of the American Chemical Society · doi:10.1021/ja9003377 · Cited by 278
Chen, H.-Y., Huang, B.-H., & Lin, C.-C. (2005) · Macromolecules · doi:10.1021/ma050672f · Cited by 166
Thevenon, A., Romain, C., Bennington, M. S., White, A. J. P., Davidson, H. J., Brooker, S., & Williams, C. K. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201602930 · Cited by 151
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Metadata
- Authors
- Dove, A. P., Gibson, V. C., Marshall, E. L., White, A. J. P., & Williams, D. J.
- Venue
- Dalton Trans.
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2004
- Issue
- 4
- Pages
- 570-578
- ISSN
- 1477-9226 (ISSN-L)
- 1477-9234
- OpenAlex
- W2025565920
- Cited by
- 192
- References
- 1
- FWCI
- 5.30
- Type
- journal article
- Language
- en
- Open access
- closed
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- Dove, A. P., Gibson, V. C., Marshall, E. L., White, A. J. P., & Williams, D. J. (2004). Magnesium and zinc complexes of a potentially tridentate β-diketiminate ligand. Dalton Trans. https://doi.org/10.1039/b314760f
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