Aluminum complexes containing cyclohexane-1,2-diyl linked bis(ketiminato) ligands and proton-promoted demethylation

Chun Hsueh Huang, Li Feng Hsueh, Pei Cheng Kuo, Man Lee Hon, Chia Liang Uno, Jui Hsien Huang, Cheng Yi Tu, Ching Han Hu, Gene Hsiang Lee, Cheng Hsiung Hung

Research output: Contribution to journalArticle

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Abstract

A series of cyclohexane-1,2-diyl linked bis(ketiminato)aluminum complexes were synthesized. Reaction of a mixture of cis- and trans-diaminocyclohexane and 2,4-pentanedione gave a mixture of cis- and trans-cyclohexane-1,2-diyl linked bis(ketimine) ligands (cis-1 and trans-1), which can be separated by fractional recrystallization. Reactions of trans-1 with 1 and 2 equiv. AlMe3 gave monoaluminum complex trans-C6H10[(NCMeCHCMeO)AlMe 2](NHCMeCHCMeO) (2) and dialuminum complex trans-C6H 10[(NCMeCHCMeO)AlMe2]2 (3), respectively. Contrarily, when 1 equiv. or excess cis-1 reacted with AlMe3, only five-coordinate, linked bis(ketiminato) aluminum complex cis-C6H 10[(NCMeCHCMeO)2AlMe] (4) could be isolated in moderate yield. Heating complex 2 at reflux in a toluene solution resulted in the elimination of 1 equiv. methane to generate a five-coordinate, linked bis-(ketiminato)aluminum complex, trans-C6H10[(NCMeCHCMeO) 2AlMe] (5). Complex 2 reacts with allyl alcohol and 2,6-dimethylphenol to form dimeric aluminum complexes [trans-C6H 10(NCMeCHCMeO)2Al]2(μ-O-CH 2CH=CH2)2 (6) and trans-C6H 10(NCMeCHCMeO)2Al(O-C6H3-2,6-Me 2) (7), respectively. All the complexes have been characterized by 1H and 13C NMR spectroscopy and X-ray diffractometry.

Original languageEnglish
Pages (from-to)3000-3008
Number of pages9
JournalEuropean Journal of Inorganic Chemistry
Issue number19
DOIs
Publication statusPublished - 2008 Jul 1

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Aluminum
Protons
Ligands
Methane
Toluene
X ray diffraction analysis
Nuclear magnetic resonance spectroscopy
Heating
Cyclohexane

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

Cite this

Huang, Chun Hsueh ; Hsueh, Li Feng ; Kuo, Pei Cheng ; Hon, Man Lee ; Uno, Chia Liang ; Huang, Jui Hsien ; Tu, Cheng Yi ; Hu, Ching Han ; Lee, Gene Hsiang ; Hung, Cheng Hsiung. / Aluminum complexes containing cyclohexane-1,2-diyl linked bis(ketiminato) ligands and proton-promoted demethylation. In: European Journal of Inorganic Chemistry. 2008 ; No. 19. pp. 3000-3008.
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title = "Aluminum complexes containing cyclohexane-1,2-diyl linked bis(ketiminato) ligands and proton-promoted demethylation",
abstract = "A series of cyclohexane-1,2-diyl linked bis(ketiminato)aluminum complexes were synthesized. Reaction of a mixture of cis- and trans-diaminocyclohexane and 2,4-pentanedione gave a mixture of cis- and trans-cyclohexane-1,2-diyl linked bis(ketimine) ligands (cis-1 and trans-1), which can be separated by fractional recrystallization. Reactions of trans-1 with 1 and 2 equiv. AlMe3 gave monoaluminum complex trans-C6H10[(NCMeCHCMeO)AlMe 2](NHCMeCHCMeO) (2) and dialuminum complex trans-C6H 10[(NCMeCHCMeO)AlMe2]2 (3), respectively. Contrarily, when 1 equiv. or excess cis-1 reacted with AlMe3, only five-coordinate, linked bis(ketiminato) aluminum complex cis-C6H 10[(NCMeCHCMeO)2AlMe] (4) could be isolated in moderate yield. Heating complex 2 at reflux in a toluene solution resulted in the elimination of 1 equiv. methane to generate a five-coordinate, linked bis-(ketiminato)aluminum complex, trans-C6H10[(NCMeCHCMeO) 2AlMe] (5). Complex 2 reacts with allyl alcohol and 2,6-dimethylphenol to form dimeric aluminum complexes [trans-C6H 10(NCMeCHCMeO)2Al]2(μ-O-CH 2CH=CH2)2 (6) and trans-C6H 10(NCMeCHCMeO)2Al(O-C6H3-2,6-Me 2) (7), respectively. All the complexes have been characterized by 1H and 13C NMR spectroscopy and X-ray diffractometry.",
author = "Huang, {Chun Hsueh} and Hsueh, {Li Feng} and Kuo, {Pei Cheng} and Hon, {Man Lee} and Uno, {Chia Liang} and Huang, {Jui Hsien} and Tu, {Cheng Yi} and Hu, {Ching Han} and Lee, {Gene Hsiang} and Hung, {Cheng Hsiung}",
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Aluminum complexes containing cyclohexane-1,2-diyl linked bis(ketiminato) ligands and proton-promoted demethylation. / Huang, Chun Hsueh; Hsueh, Li Feng; Kuo, Pei Cheng; Hon, Man Lee; Uno, Chia Liang; Huang, Jui Hsien; Tu, Cheng Yi; Hu, Ching Han; Lee, Gene Hsiang; Hung, Cheng Hsiung.

In: European Journal of Inorganic Chemistry, No. 19, 01.07.2008, p. 3000-3008.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Aluminum complexes containing cyclohexane-1,2-diyl linked bis(ketiminato) ligands and proton-promoted demethylation

AU - Huang, Chun Hsueh

AU - Hsueh, Li Feng

AU - Kuo, Pei Cheng

AU - Hon, Man Lee

AU - Uno, Chia Liang

AU - Huang, Jui Hsien

AU - Tu, Cheng Yi

AU - Hu, Ching Han

AU - Lee, Gene Hsiang

AU - Hung, Cheng Hsiung

PY - 2008/7/1

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N2 - A series of cyclohexane-1,2-diyl linked bis(ketiminato)aluminum complexes were synthesized. Reaction of a mixture of cis- and trans-diaminocyclohexane and 2,4-pentanedione gave a mixture of cis- and trans-cyclohexane-1,2-diyl linked bis(ketimine) ligands (cis-1 and trans-1), which can be separated by fractional recrystallization. Reactions of trans-1 with 1 and 2 equiv. AlMe3 gave monoaluminum complex trans-C6H10[(NCMeCHCMeO)AlMe 2](NHCMeCHCMeO) (2) and dialuminum complex trans-C6H 10[(NCMeCHCMeO)AlMe2]2 (3), respectively. Contrarily, when 1 equiv. or excess cis-1 reacted with AlMe3, only five-coordinate, linked bis(ketiminato) aluminum complex cis-C6H 10[(NCMeCHCMeO)2AlMe] (4) could be isolated in moderate yield. Heating complex 2 at reflux in a toluene solution resulted in the elimination of 1 equiv. methane to generate a five-coordinate, linked bis-(ketiminato)aluminum complex, trans-C6H10[(NCMeCHCMeO) 2AlMe] (5). Complex 2 reacts with allyl alcohol and 2,6-dimethylphenol to form dimeric aluminum complexes [trans-C6H 10(NCMeCHCMeO)2Al]2(μ-O-CH 2CH=CH2)2 (6) and trans-C6H 10(NCMeCHCMeO)2Al(O-C6H3-2,6-Me 2) (7), respectively. All the complexes have been characterized by 1H and 13C NMR spectroscopy and X-ray diffractometry.

AB - A series of cyclohexane-1,2-diyl linked bis(ketiminato)aluminum complexes were synthesized. Reaction of a mixture of cis- and trans-diaminocyclohexane and 2,4-pentanedione gave a mixture of cis- and trans-cyclohexane-1,2-diyl linked bis(ketimine) ligands (cis-1 and trans-1), which can be separated by fractional recrystallization. Reactions of trans-1 with 1 and 2 equiv. AlMe3 gave monoaluminum complex trans-C6H10[(NCMeCHCMeO)AlMe 2](NHCMeCHCMeO) (2) and dialuminum complex trans-C6H 10[(NCMeCHCMeO)AlMe2]2 (3), respectively. Contrarily, when 1 equiv. or excess cis-1 reacted with AlMe3, only five-coordinate, linked bis(ketiminato) aluminum complex cis-C6H 10[(NCMeCHCMeO)2AlMe] (4) could be isolated in moderate yield. Heating complex 2 at reflux in a toluene solution resulted in the elimination of 1 equiv. methane to generate a five-coordinate, linked bis-(ketiminato)aluminum complex, trans-C6H10[(NCMeCHCMeO) 2AlMe] (5). Complex 2 reacts with allyl alcohol and 2,6-dimethylphenol to form dimeric aluminum complexes [trans-C6H 10(NCMeCHCMeO)2Al]2(μ-O-CH 2CH=CH2)2 (6) and trans-C6H 10(NCMeCHCMeO)2Al(O-C6H3-2,6-Me 2) (7), respectively. All the complexes have been characterized by 1H and 13C NMR spectroscopy and X-ray diffractometry.

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