Reactions of (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline with diethylzinc: Synthesis, characterization and catalytic studies for ring-opening polymerization of ε-caprolactone

Chao Hsiang Wang; Chen Yu Li; Chia Her Lin; Yi Chang Liu; Bao Tsan Ko

doi:10.1016/j.inoche.2011.05.046

Reactions of (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline with diethylzinc: Synthesis, characterization and catalytic studies for ring-opening polymerization of ε-caprolactone

Chao Hsiang Wang, Chen Yu Li, Chia Her Lin, Yi Chang Liu, Bao Tsan Ko^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

Zinc complexes supported by NN-bidentate AA^Bn ligand (AA ^Bn-H = (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline) are synthesized and fully characterized. The reaction of diethyl zinc (ZnEt ₂) with AA^Bn-H (1.1 mol equiv) yields three-coordinated mono-adduct zinc complex [(AA^Bn)ZnEt] (1). However, treatment of AA^Bn-H with ZnEt₂ in the same stoichiometric proportion in the presence of 4-dimethylaminopyridine (DMAP, one equiv) affords [(AA ^Bn)Zn(DMAP)Et] (2) as the tetra-coordinated monomeric zinc complex. Bis-adduct complex [(AA^Bn)₂Zn] (3) results from treatment of ZnEt₂ with AA^Bn-H (two equiv) in refluxing toluene in high yield. Complexes 1 and 3 are efficient catalysts for the ring-opening polymerization (ROP) of ε-caprolactone (ε-CL) in the presence of alcohol. The "controlled" character of Zn complex 1 also enabled preparation of the PEG-b-PCL copolymer.

Original language	English
Pages (from-to)	1456-1460
Number of pages	5
Journal	Inorganic Chemistry Communications
Volume	14
Issue number	9
DOIs	https://doi.org/10.1016/j.inoche.2011.05.046
Publication status	Published - 2011 Sept
Externally published	Yes

Keywords

Anilido-aldimine
Catalyst
NN-bidentate
Ring-opening polymerization
Zinc complex
ε-caprolactone

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.inoche.2011.05.046

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Reactions of (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline with diethylzinc: Synthesis, characterization and catalytic studies for ring-opening polymerization of ε-caprolactone. / Wang, Chao Hsiang; Li, Chen Yu; Lin, Chia Her et al.
In: Inorganic Chemistry Communications, Vol. 14, No. 9, 09.2011, p. 1456-1460.

Research output: Contribution to journal › Article › peer-review

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title = "Reactions of (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline with diethylzinc: Synthesis, characterization and catalytic studies for ring-opening polymerization of ε-caprolactone",

abstract = "Zinc complexes supported by NN-bidentate AABn ligand (AA Bn-H = (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline) are synthesized and fully characterized. The reaction of diethyl zinc (ZnEt 2) with AABn-H (1.1 mol equiv) yields three-coordinated mono-adduct zinc complex [(AABn)ZnEt] (1). However, treatment of AABn-H with ZnEt2 in the same stoichiometric proportion in the presence of 4-dimethylaminopyridine (DMAP, one equiv) affords [(AA Bn)Zn(DMAP)Et] (2) as the tetra-coordinated monomeric zinc complex. Bis-adduct complex [(AABn)2Zn] (3) results from treatment of ZnEt2 with AABn-H (two equiv) in refluxing toluene in high yield. Complexes 1 and 3 are efficient catalysts for the ring-opening polymerization (ROP) of ε-caprolactone (ε-CL) in the presence of alcohol. The {"}controlled{"} character of Zn complex 1 also enabled preparation of the PEG-b-PCL copolymer.",

keywords = "Anilido-aldimine, Catalyst, NN-bidentate, Ring-opening polymerization, Zinc complex, ε-caprolactone",

author = "Wang, {Chao Hsiang} and Li, {Chen Yu} and Lin, {Chia Her} and Liu, {Yi Chang} and Ko, {Bao Tsan}",

note = "Funding Information: We gratefully acknowledge the financial support from the National Science Council, Taiwan ( NSC99-2113-M-033-007-MY2 ). ",

year = "2011",

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doi = "10.1016/j.inoche.2011.05.046",

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T1 - Reactions of (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline with diethylzinc

T2 - Synthesis, characterization and catalytic studies for ring-opening polymerization of ε-caprolactone

AU - Wang, Chao Hsiang

AU - Li, Chen Yu

AU - Lin, Chia Her

AU - Liu, Yi Chang

AU - Ko, Bao Tsan

N1 - Funding Information: We gratefully acknowledge the financial support from the National Science Council, Taiwan ( NSC99-2113-M-033-007-MY2 ).

PY - 2011/9

Y1 - 2011/9

N2 - Zinc complexes supported by NN-bidentate AABn ligand (AA Bn-H = (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline) are synthesized and fully characterized. The reaction of diethyl zinc (ZnEt 2) with AABn-H (1.1 mol equiv) yields three-coordinated mono-adduct zinc complex [(AABn)ZnEt] (1). However, treatment of AABn-H with ZnEt2 in the same stoichiometric proportion in the presence of 4-dimethylaminopyridine (DMAP, one equiv) affords [(AA Bn)Zn(DMAP)Et] (2) as the tetra-coordinated monomeric zinc complex. Bis-adduct complex [(AABn)2Zn] (3) results from treatment of ZnEt2 with AABn-H (two equiv) in refluxing toluene in high yield. Complexes 1 and 3 are efficient catalysts for the ring-opening polymerization (ROP) of ε-caprolactone (ε-CL) in the presence of alcohol. The "controlled" character of Zn complex 1 also enabled preparation of the PEG-b-PCL copolymer.

AB - Zinc complexes supported by NN-bidentate AABn ligand (AA Bn-H = (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline) are synthesized and fully characterized. The reaction of diethyl zinc (ZnEt 2) with AABn-H (1.1 mol equiv) yields three-coordinated mono-adduct zinc complex [(AABn)ZnEt] (1). However, treatment of AABn-H with ZnEt2 in the same stoichiometric proportion in the presence of 4-dimethylaminopyridine (DMAP, one equiv) affords [(AA Bn)Zn(DMAP)Et] (2) as the tetra-coordinated monomeric zinc complex. Bis-adduct complex [(AABn)2Zn] (3) results from treatment of ZnEt2 with AABn-H (two equiv) in refluxing toluene in high yield. Complexes 1 and 3 are efficient catalysts for the ring-opening polymerization (ROP) of ε-caprolactone (ε-CL) in the presence of alcohol. The "controlled" character of Zn complex 1 also enabled preparation of the PEG-b-PCL copolymer.

KW - Anilido-aldimine

KW - Catalyst

KW - NN-bidentate

KW - Ring-opening polymerization

KW - Zinc complex

KW - ε-caprolactone

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Reactions of (E)-N-[2-(benzyliminomethyl)phenyl]-2,6-diisopropylaniline with diethylzinc: Synthesis, characterization and catalytic studies for ring-opening polymerization of ε-caprolactone

Abstract

Keywords

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