Aluminum compounds containing η1- and/or η5-bidentate dianionic pyrrolyl-methylamide ligands

Ya Chi Chen, Che Yu Lin, Chun Yin Li, Jui-Hsien Huang, Ling Chueh Chang, Ting Yu Lee

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Abstract

A series of dialuminum compounds have been synthesized and their reactivity and application for lactide polymerization have been studied. The reaction of AlH3·NMe3 with [C4H3NH(2- CH2NHtBu)] in diethyl ether generated a dimeric aluminum hydride compound, [{[C4H3N(2-CH2NtBu)]AlH}2] (1). The structure of 1 was confirmed by spectroscopy of a deuterated analogue of 1 with an Al-D function. Direct treatment of [C4H 3NH(2-CH2NHtBu)] with LiAlH4 in diethyl ether resulted in colorless crystals of [{Li[μ-η15- C4H3N(2-CH2NtBu)]2Al}2] (2) in 80% yield after recrystallization from a toluene solution. The μ-η15-pyrrolyl protons exhibit high-field shifts at δ=5.73, 6.15, and 6.72 comparable to a similar η5-bonding mode in the literature. Treatment of 1 with 1 equiv acetone oxime or acetone in dichloromethane gave [{[C4H 3N(2-CH2NtBu)]Al-[κO,κN-(ON=CMe 2)]}2] (3) and [{[C4H3N(2-CH 2NtBu)]Al(O-CHMe2)}2] (4) in 67% and 60% yield, respectively. Compounds 1-4 have been characterized by X-ray diffractometry and were used as catalysts for ε-caprolactone polymerization.

Original languageEnglish
Pages (from-to)9747-9753
Number of pages7
JournalChemistry - A European Journal
Volume14
Issue number31
DOIs
Publication statusPublished - 2008 Oct 29

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Aluminum Compounds
Aluminum compounds
Acetone
Ether
Ethers
Ligands
Polymerization
Methylene Chloride
Dichloromethane
Toluene
Aluminum
Hydrides
X ray diffraction analysis
Protons
Spectroscopy
Crystals
Catalysts

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Chen, Ya Chi ; Lin, Che Yu ; Li, Chun Yin ; Huang, Jui-Hsien ; Chang, Ling Chueh ; Lee, Ting Yu. / Aluminum compounds containing η1- and/or η5-bidentate dianionic pyrrolyl-methylamide ligands. In: Chemistry - A European Journal. 2008 ; Vol. 14, No. 31. pp. 9747-9753.
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title = "Aluminum compounds containing η1- and/or η5-bidentate dianionic pyrrolyl-methylamide ligands",
abstract = "A series of dialuminum compounds have been synthesized and their reactivity and application for lactide polymerization have been studied. The reaction of AlH3·NMe3 with [C4H3NH(2- CH2NHtBu)] in diethyl ether generated a dimeric aluminum hydride compound, [{[C4H3N(2-CH2NtBu)]AlH}2] (1). The structure of 1 was confirmed by spectroscopy of a deuterated analogue of 1 with an Al-D function. Direct treatment of [C4H 3NH(2-CH2NHtBu)] with LiAlH4 in diethyl ether resulted in colorless crystals of [{Li[μ-η1:η5- C4H3N(2-CH2NtBu)]2Al}2] (2) in 80{\%} yield after recrystallization from a toluene solution. The μ-η1:η5-pyrrolyl protons exhibit high-field shifts at δ=5.73, 6.15, and 6.72 comparable to a similar η5-bonding mode in the literature. Treatment of 1 with 1 equiv acetone oxime or acetone in dichloromethane gave [{[C4H 3N(2-CH2NtBu)]Al-[κO,κN-(ON=CMe 2)]}2] (3) and [{[C4H3N(2-CH 2NtBu)]Al(O-CHMe2)}2] (4) in 67{\%} and 60{\%} yield, respectively. Compounds 1-4 have been characterized by X-ray diffractometry and were used as catalysts for ε-caprolactone polymerization.",
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Aluminum compounds containing η1- and/or η5-bidentate dianionic pyrrolyl-methylamide ligands. / Chen, Ya Chi; Lin, Che Yu; Li, Chun Yin; Huang, Jui-Hsien; Chang, Ling Chueh; Lee, Ting Yu.

In: Chemistry - A European Journal, Vol. 14, No. 31, 29.10.2008, p. 9747-9753.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Aluminum compounds containing η1- and/or η5-bidentate dianionic pyrrolyl-methylamide ligands

AU - Chen, Ya Chi

AU - Lin, Che Yu

AU - Li, Chun Yin

AU - Huang, Jui-Hsien

AU - Chang, Ling Chueh

AU - Lee, Ting Yu

PY - 2008/10/29

Y1 - 2008/10/29

N2 - A series of dialuminum compounds have been synthesized and their reactivity and application for lactide polymerization have been studied. The reaction of AlH3·NMe3 with [C4H3NH(2- CH2NHtBu)] in diethyl ether generated a dimeric aluminum hydride compound, [{[C4H3N(2-CH2NtBu)]AlH}2] (1). The structure of 1 was confirmed by spectroscopy of a deuterated analogue of 1 with an Al-D function. Direct treatment of [C4H 3NH(2-CH2NHtBu)] with LiAlH4 in diethyl ether resulted in colorless crystals of [{Li[μ-η1:η5- C4H3N(2-CH2NtBu)]2Al}2] (2) in 80% yield after recrystallization from a toluene solution. The μ-η1:η5-pyrrolyl protons exhibit high-field shifts at δ=5.73, 6.15, and 6.72 comparable to a similar η5-bonding mode in the literature. Treatment of 1 with 1 equiv acetone oxime or acetone in dichloromethane gave [{[C4H 3N(2-CH2NtBu)]Al-[κO,κN-(ON=CMe 2)]}2] (3) and [{[C4H3N(2-CH 2NtBu)]Al(O-CHMe2)}2] (4) in 67% and 60% yield, respectively. Compounds 1-4 have been characterized by X-ray diffractometry and were used as catalysts for ε-caprolactone polymerization.

AB - A series of dialuminum compounds have been synthesized and their reactivity and application for lactide polymerization have been studied. The reaction of AlH3·NMe3 with [C4H3NH(2- CH2NHtBu)] in diethyl ether generated a dimeric aluminum hydride compound, [{[C4H3N(2-CH2NtBu)]AlH}2] (1). The structure of 1 was confirmed by spectroscopy of a deuterated analogue of 1 with an Al-D function. Direct treatment of [C4H 3NH(2-CH2NHtBu)] with LiAlH4 in diethyl ether resulted in colorless crystals of [{Li[μ-η1:η5- C4H3N(2-CH2NtBu)]2Al}2] (2) in 80% yield after recrystallization from a toluene solution. The μ-η1:η5-pyrrolyl protons exhibit high-field shifts at δ=5.73, 6.15, and 6.72 comparable to a similar η5-bonding mode in the literature. Treatment of 1 with 1 equiv acetone oxime or acetone in dichloromethane gave [{[C4H 3N(2-CH2NtBu)]Al-[κO,κN-(ON=CMe 2)]}2] (3) and [{[C4H3N(2-CH 2NtBu)]Al(O-CHMe2)}2] (4) in 67% and 60% yield, respectively. Compounds 1-4 have been characterized by X-ray diffractometry and were used as catalysts for ε-caprolactone polymerization.

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