Synthesis and characterization of dialkylaluminum amidates and their ring-opening polymerization of ε-caprolactone

Zhang, Wenjuan; Wang, Youhong; Cao, Ji; Wang, Lin; Pan, Yi; Redshaw, Carl; Sun, Wen Hua

Abstract

The stoichiometric reactions of N-(2-methylquinolin-8-yl) (R)amides (L1-L8; L1, R = Ph; L2, R = p-FPh; L3, R = p-ClPh; L4, R = p-(MeO)Ph; L5, R = o-MePh; L6, R = p-MePh; L7, R = Me; L8, R = CF3) with Me3Al afforded the corresponding dimethylaluminum amidate complexes [Me 2AlL] (C1-C8). The treatment of N-(2-methylquinolin-8-yl)picolinamide (L9) with 1 or 2 equiv of Me3Al formed Me2AlL9 (C9) or Me2AlL9·Me3Al (C10), respectively; meanwhile, the stoichiometric reaction of L9 with iBu3Al gave iBu2AlL9 (C11). All organoaluminum amidate complexes were fully characterized by 1H/13C NMR spectroscopy and elemental analysis, and the unambiguous structures of complexes C2, C4, C9, and C11 were further determined by single-crystal X-ray diffraction. With the assistance of 1 equiv of BnOH, all dialkylaluminum amidate complexes showed appreciable activities toward the ring-opening polymerization of ε-caprolactone and produced polycaprolactones with narrow polydispersity; the nature of the active species was also investigated. © 2011 American Chemical Society.

Citation

Zhang, W., Wang, Y., Cao, J., Wang, L., Pan, Y., Redshaw, C., & Sun, W. H. (2011). Synthesis and characterization of dialkylaluminum amidates and their ring-opening polymerization of ε-caprolactone. Organometallics, 30(22), 6253-6261. https://doi.org/10.1021/om2008343

• Journal Article Type: Article
• Online Publication Date: Nov 4, 2011
• Publication Date: Nov 28, 2011
• Deposit Date: Jun 8, 2022
• Journal: Organometallics
• Print ISSN: 0276-7333
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 30
• Issue: 22
• Pages: 6253-6261
• DOI: https://doi.org/10.1021/om2008343
• Public URL: https://hull-repository.worktribe.com/output/3622335