Magnesium complexes containing η1- and η3- pyrrolyl or ketiminato ligands: Synthesis, structural investigation and ε-caprolactone ring-opening polymerisation

Li Feng Hsueh, Nien Tsu Chuang, Cheng Yuan Lee, Amitabha Datta, Jui Hsien Huang, Ting Yu Lee

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A series of dimeric magnesium derivatives containing substituted pyrrolyl or ketiminato ligands was synthesised and the application of these derivatives for the ring opening polymerisation of ε-caprolactone has been carried out. Reactions of [Mg{N(SiMe3)2}]2 (1) with one equiv. of 2-dimethylaminomethyl pyrrole and 2-diethylaminomethyl pyrrole in toluene generates [Mg{C4H3N(2-CH2NMe 2)}{N(SiMe3)2}]2 (2) and [Mg{C 4H3N(2-CH2NEt2)}{N(SiMe 3)2}]2 (3), respectively, in high yield. Similarly, the reaction of 1 with one equiv. of 2-tert-butylaminomethyl pyrrole in toluene at room temperature affords [Mg{C4H3N(2-CH 2NHtBu)}{N(SiMe3)2}]2 (4). Furthermore, reactions of 1 with one equiv. of HOCMeCHCMeN(C6H 3-2,6-iPr2) or HOCMeCHCMeN(C6H 4-2-OMe) in toluene yielded the dimeric magnesium complexes, [Mg{OCMeCHCMeN(C6H3-2,6-iPr2)}{N(SiMe 3)2}]2 (5) and [Mg{OCMeCHCMeN(C 6H4-2-OMe)}{N(SiMe3)2}]2 (6), respectively, in satisfactory yields by means of deamination. All the complexes were characterised by NMR spectroscopy and X-ray diffraction analysis in the solid state. They show moderate reactivity towards the ring opening polymerisation of ε-caprolactone in dichloromethane or tetrahydrofuran. A series of dimeric magnesium derivatives containing substituted pyrrolyl or ketiminato ligands was synthesised and the compounds were evaluated as catalytic precursors. The complexes show moderate reactivity towards the ring opening polymerisation of ε-caprolactone in dichloromethane or tetrahydrofuran.

Original languageEnglish
Pages (from-to)5530-5537
Number of pages8
JournalEuropean Journal of Inorganic Chemistry
Issue number36
DOIs
Publication statusPublished - 2011 Dec 1

Fingerprint

Pyrroles
Ring opening polymerization
Toluene
Magnesium
Methylene Chloride
Ligands
Derivatives
X ray diffraction analysis
Nuclear magnetic resonance spectroscopy
caprolactone
Temperature
tetrahydrofuran

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

Cite this

@article{958e8cfb59ea45a4b1922b5c25fd6c1d,
title = "Magnesium complexes containing η1- and η3- pyrrolyl or ketiminato ligands: Synthesis, structural investigation and ε-caprolactone ring-opening polymerisation",
abstract = "A series of dimeric magnesium derivatives containing substituted pyrrolyl or ketiminato ligands was synthesised and the application of these derivatives for the ring opening polymerisation of ε-caprolactone has been carried out. Reactions of [Mg{N(SiMe3)2}]2 (1) with one equiv. of 2-dimethylaminomethyl pyrrole and 2-diethylaminomethyl pyrrole in toluene generates [Mg{C4H3N(2-CH2NMe 2)}{N(SiMe3)2}]2 (2) and [Mg{C 4H3N(2-CH2NEt2)}{N(SiMe 3)2}]2 (3), respectively, in high yield. Similarly, the reaction of 1 with one equiv. of 2-tert-butylaminomethyl pyrrole in toluene at room temperature affords [Mg{C4H3N(2-CH 2NHtBu)}{N(SiMe3)2}]2 (4). Furthermore, reactions of 1 with one equiv. of HOCMeCHCMeN(C6H 3-2,6-iPr2) or HOCMeCHCMeN(C6H 4-2-OMe) in toluene yielded the dimeric magnesium complexes, [Mg{OCMeCHCMeN(C6H3-2,6-iPr2)}{N(SiMe 3)2}]2 (5) and [Mg{OCMeCHCMeN(C 6H4-2-OMe)}{N(SiMe3)2}]2 (6), respectively, in satisfactory yields by means of deamination. All the complexes were characterised by NMR spectroscopy and X-ray diffraction analysis in the solid state. They show moderate reactivity towards the ring opening polymerisation of ε-caprolactone in dichloromethane or tetrahydrofuran. A series of dimeric magnesium derivatives containing substituted pyrrolyl or ketiminato ligands was synthesised and the compounds were evaluated as catalytic precursors. The complexes show moderate reactivity towards the ring opening polymerisation of ε-caprolactone in dichloromethane or tetrahydrofuran.",
author = "Hsueh, {Li Feng} and Chuang, {Nien Tsu} and Lee, {Cheng Yuan} and Amitabha Datta and Huang, {Jui Hsien} and Lee, {Ting Yu}",
year = "2011",
month = "12",
day = "1",
doi = "10.1002/ejic.201100827",
language = "English",
pages = "5530--5537",
journal = "Chemische Berichte",
issn = "0009-2940",
publisher = "Wiley-VCH Verlag",
number = "36",

}

Magnesium complexes containing η1- and η3- pyrrolyl or ketiminato ligands : Synthesis, structural investigation and ε-caprolactone ring-opening polymerisation. / Hsueh, Li Feng; Chuang, Nien Tsu; Lee, Cheng Yuan; Datta, Amitabha; Huang, Jui Hsien; Lee, Ting Yu.

In: European Journal of Inorganic Chemistry, No. 36, 01.12.2011, p. 5530-5537.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Magnesium complexes containing η1- and η3- pyrrolyl or ketiminato ligands

T2 - Synthesis, structural investigation and ε-caprolactone ring-opening polymerisation

AU - Hsueh, Li Feng

AU - Chuang, Nien Tsu

AU - Lee, Cheng Yuan

AU - Datta, Amitabha

AU - Huang, Jui Hsien

AU - Lee, Ting Yu

PY - 2011/12/1

Y1 - 2011/12/1

N2 - A series of dimeric magnesium derivatives containing substituted pyrrolyl or ketiminato ligands was synthesised and the application of these derivatives for the ring opening polymerisation of ε-caprolactone has been carried out. Reactions of [Mg{N(SiMe3)2}]2 (1) with one equiv. of 2-dimethylaminomethyl pyrrole and 2-diethylaminomethyl pyrrole in toluene generates [Mg{C4H3N(2-CH2NMe 2)}{N(SiMe3)2}]2 (2) and [Mg{C 4H3N(2-CH2NEt2)}{N(SiMe 3)2}]2 (3), respectively, in high yield. Similarly, the reaction of 1 with one equiv. of 2-tert-butylaminomethyl pyrrole in toluene at room temperature affords [Mg{C4H3N(2-CH 2NHtBu)}{N(SiMe3)2}]2 (4). Furthermore, reactions of 1 with one equiv. of HOCMeCHCMeN(C6H 3-2,6-iPr2) or HOCMeCHCMeN(C6H 4-2-OMe) in toluene yielded the dimeric magnesium complexes, [Mg{OCMeCHCMeN(C6H3-2,6-iPr2)}{N(SiMe 3)2}]2 (5) and [Mg{OCMeCHCMeN(C 6H4-2-OMe)}{N(SiMe3)2}]2 (6), respectively, in satisfactory yields by means of deamination. All the complexes were characterised by NMR spectroscopy and X-ray diffraction analysis in the solid state. They show moderate reactivity towards the ring opening polymerisation of ε-caprolactone in dichloromethane or tetrahydrofuran. A series of dimeric magnesium derivatives containing substituted pyrrolyl or ketiminato ligands was synthesised and the compounds were evaluated as catalytic precursors. The complexes show moderate reactivity towards the ring opening polymerisation of ε-caprolactone in dichloromethane or tetrahydrofuran.

AB - A series of dimeric magnesium derivatives containing substituted pyrrolyl or ketiminato ligands was synthesised and the application of these derivatives for the ring opening polymerisation of ε-caprolactone has been carried out. Reactions of [Mg{N(SiMe3)2}]2 (1) with one equiv. of 2-dimethylaminomethyl pyrrole and 2-diethylaminomethyl pyrrole in toluene generates [Mg{C4H3N(2-CH2NMe 2)}{N(SiMe3)2}]2 (2) and [Mg{C 4H3N(2-CH2NEt2)}{N(SiMe 3)2}]2 (3), respectively, in high yield. Similarly, the reaction of 1 with one equiv. of 2-tert-butylaminomethyl pyrrole in toluene at room temperature affords [Mg{C4H3N(2-CH 2NHtBu)}{N(SiMe3)2}]2 (4). Furthermore, reactions of 1 with one equiv. of HOCMeCHCMeN(C6H 3-2,6-iPr2) or HOCMeCHCMeN(C6H 4-2-OMe) in toluene yielded the dimeric magnesium complexes, [Mg{OCMeCHCMeN(C6H3-2,6-iPr2)}{N(SiMe 3)2}]2 (5) and [Mg{OCMeCHCMeN(C 6H4-2-OMe)}{N(SiMe3)2}]2 (6), respectively, in satisfactory yields by means of deamination. All the complexes were characterised by NMR spectroscopy and X-ray diffraction analysis in the solid state. They show moderate reactivity towards the ring opening polymerisation of ε-caprolactone in dichloromethane or tetrahydrofuran. A series of dimeric magnesium derivatives containing substituted pyrrolyl or ketiminato ligands was synthesised and the compounds were evaluated as catalytic precursors. The complexes show moderate reactivity towards the ring opening polymerisation of ε-caprolactone in dichloromethane or tetrahydrofuran.

UR - http://www.scopus.com/inward/record.url?scp=83755178307&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=83755178307&partnerID=8YFLogxK

U2 - 10.1002/ejic.201100827

DO - 10.1002/ejic.201100827

M3 - Article

AN - SCOPUS:83755178307

SP - 5530

EP - 5537

JO - Chemische Berichte

JF - Chemische Berichte

SN - 0009-2940

IS - 36

ER -