Synthesis and characterization of tri-dentate pyrrole-morpholine ligands and their corresponding aluminum, magnesium, and zinc compounds

Chien, Kai Min; Hu, Ting; Lin, Chia Her; Lo, Ya Chun; Lee, Ting Yu; Huang, Jui Hsien

doi:10.1016/j.jorganchem.2014.12.018

Cited by 10 publications

(1 citation statement)

References 37 publications

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“…The polymers were analyzed on the basis of 1 H NMR spectra and gel permeation chromatography (GPC). As shown in entry 10, Table 1 , the optimal conditions for the ring-opening polymerization of ε-caprolactone are the simultaneous addition of toluene as solvent and benzyl alcohol (BnOH) as co-catalyst at 80 °C for 1 h. These results are in agreement with reports in both the existing literature [ 44 , 45 ] and our previously published papers [ 46 , 47 ] that metal alkoxides are better initiators then metal alkyls for the ring-opening polymerization of cyclic esters. According to the practical data given in Table 2 , compounds 1 ~ 4 all manifest promising activities for the ring-opening polymerization of ε-caprolactone at 80 °C and 1 h reaction time, with a conversion rate of ca.…”

Section: Resultssupporting

confidence: 90%

Ring-Opening Polymerization of ε-Caprolactone and Styrene Oxide–CO2 Coupling Reactions Catalyzed by Chelated Dehydroacetic Acid–Imine Aluminum Complexes

Wang

et al. 2021

Molecules

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A series of chelated dehydroacetic acid–imine-based ligands L1H~L4H was synthesized by reacting dehydroacetic acid with 2-t-butylaniline, (S)-1-phenyl-ethylamine, 4-methoxylbenzylamine, and 2-(aminoethyl)pyridine, respectively, in moderate yields. Ligands L1H~L4H reacted with AlMe3 in toluene to afford corresponding compounds AlMe2L1 (1), AlMe2L2 (2), AlMe2L3 (3), and AlMe2L4 (4). All the ligands and aluminum compounds were characterized by IR spectra, 1H and 13C NMR spectroscopy. Additionally, the ligands L1H~L4H and corresponding aluminum derivatives 1, 3, and 4 were characterized by single-crystal X-ray diffractometry. The catalytic activities using these aluminum compounds as catalysts for the ε-caprolactone ring-opening polymerization (ROP) and styrene oxide-CO2 coupling reactions were studied. The results show that increases in the reaction temperature and selective solvent intensify the conversions of ε-caprolactone to polycaprolactone. Regarding the coupling reactions of styrene oxide and CO2, the conversion rate is over 90% for a period of 12 h at 90 °C. This strategy dispenses the origination of cyclic styrene carbonates, which is an appealing concern because of the transformation of CO2 into an inexpensive, renewable and easy excess carbon feedstock.

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Section: Resultssupporting

confidence: 90%

Ring-Opening Polymerization of ε-Caprolactone and Styrene Oxide–CO2 Coupling Reactions Catalyzed by Chelated Dehydroacetic Acid–Imine Aluminum Complexes

Wang

et al. 2021

Molecules

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Thermal isomerization of ruthenium hydride compounds containing asymmetric bidentate pyrrole‐imine ligands

Lai

Chen

et al. 2019

J Chinese Chemical Soc

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A series of ruthenium hydride compounds containing substituted bidentate pyrrole‐imine ligands were synthesized and characterized. Reacting RuHCl(CO)(PPh3)3 with one equivalent of [C4H3NH(2‐CH=NR)] in ethanol in the presence of KOH gave compounds {RuH(CO)(PPh3)2[C4H3N(2‐CH=NR)]} where trans‐Py‐Ru‐H 1, R = CH2CH2C6H9; cis‐Py‐Ru‐H 2, R = Ph‐2‐Me; and cis‐Py‐Ru‐H 3, R = C6H11. Heating trans‐Py‐Ru‐H 1 in toluene at 70°C for 12 hr resulted a thermal conversion of the trans‐Py‐Ru‐H 1 into its cis form, {RuH(CO)(PPh3)2[C4H3N(2‐CH=NCH2CH2C6H9)]} (cis‐Py‐Ru‐H 1) in very high yield. The 1H NMR spectra of trans‐Py‐Ru‐H 1, cis‐Py‐Ru‐H 2, cis‐Py‐Ru‐H 3, and cis‐Py‐Ru‐H 1 all show a typical triplet at ca. δ–11 for the hydride. The trans and cis form indicate the relative positions of pyrrole ring and hydride. The geometries of trans‐Py‐Ru‐H 1, cis‐Py‐Ru‐H 1, and cis‐Py‐Ru‐H 3 are relatively similar showing typical octahedral geometries with two PPh3 fragments arranged in trans positions.

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Pyrroles and benzannulated forms

Sadimenko

2020

Organometallic Chemistry of Five-Membered Heterocycles

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Synthesis and characterization of tri-dentate pyrrole-morpholine ligands and their corresponding aluminum, magnesium, and zinc compounds

Cited by 10 publications

References 37 publications

Ring-Opening Polymerization of ε-Caprolactone and Styrene Oxide–CO2 Coupling Reactions Catalyzed by Chelated Dehydroacetic Acid–Imine Aluminum Complexes

Ring-Opening Polymerization of ε-Caprolactone and Styrene Oxide–CO2 Coupling Reactions Catalyzed by Chelated Dehydroacetic Acid–Imine Aluminum Complexes

Thermal isomerization of ruthenium hydride compounds containing asymmetric bidentate pyrrole‐imine ligands

Pyrroles and benzannulated forms

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