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

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

doi:10.1021/om2008343

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

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

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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 [Me2AlL] (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 e-caprolactone and produced polycaprolactones with narrow polydispersity; the nature of the active species was also investigated.

Original language	English
Pages (from-to)	6253-6261
Number of pages	9
Journal	Organometallics
Volume	30
Issue number	22
DOIs	https://doi.org/10.1021/om2008343
Publication status	Published - 4 Nov 2011

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10.1021/om2008343

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@article{94c1e44980d0492898962286b3ab60a4,

title = "Synthesis and characterization of dialkylaluminum amidates and their ring-opening polymerization of ε-caprolactone",

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 [Me2AlL] (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 e-caprolactone and produced polycaprolactones with narrow polydispersity; the nature of the active species was also investigated.",

author = "Wenjuan Zhang and Youhong Wang and Ji Cao and Lin Wang and Yi Pan and Carl Redshaw and Wen-Hua Sun",

year = "2011",

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doi = "10.1021/om2008343",

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T1 - Synthesis and characterization of dialkylaluminum amidates and their ring-opening polymerization of ε-caprolactone

AU - Zhang, Wenjuan

AU - Wang, Youhong

AU - Cao, Ji

AU - Wang, Lin

AU - Pan, Yi

AU - Redshaw, Carl

AU - Sun, Wen-Hua

PY - 2011/11/4

Y1 - 2011/11/4

N2 - 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 [Me2AlL] (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 e-caprolactone and produced polycaprolactones with narrow polydispersity; the nature of the active species was also investigated.

AB - 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 [Me2AlL] (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 e-caprolactone and produced polycaprolactones with narrow polydispersity; the nature of the active species was also investigated.

U2 - 10.1021/om2008343

DO - 10.1021/om2008343

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