Synthesis of Some Organometallic Compounds of 1,2-Acenaphthylenedione Dioxime and Comparision with 8<sub>12</sub>Model Compounds

Tan, Nükhet; roĝlu, Özer Bek

doi:10.1080/00945718308055877

Synthesis and Reactivity in Inorganic and Metal-Organic Chemist

1983

DOI: 10.1080/00945718308055877

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Synthesis of Some Organometallic Compounds of 1,2-Acenaphthylenedione Dioxime and Comparision with 8₁₂Model Compounds

Nükhet Tan

Özer Bek roĝlu

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Cited by 25 publications

References 14 publications

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Synthesis and Complexation of a New 14‐Membered N₂O₂ Macrocycle with vic‐Dioxime Moieties

Hamuryudan

Bekâroĝlu

1994

Chem. Ber.

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The new vic-dioxime ligand 2 (LH4) carrying a 14-membered properties of tri-and pentanuclear complexes were investi- The successful design and synthesis of ligands capable of forming multinuclear complexes are of great interest for obtaining special effects in magnetic, optical, and electrical properties. For this purpose, the ligands need to carry multidonor groups to be able to bind more than one metal ion simultaneously. Macrocyclic ligands can be considered as important candidates for one of the components of these ligands. Although many examples of macrocyclic synthetic ligands contain identical donor groups being liable to coordinate with either hard or soft metal ions, a mixture of two or more donor sites has been also employed to tune the selectivity and stabilityrll. Incorporation of a vic-dioxime moiety onto the macrocycle provides an efficient binding site for transition metal ions by formation of an MN4 core with additional two hydrogen bridged2].The high stability of the complexes prepared with vicdioxime ligands has been extensively used for various purposes including model compounds for vitamin or trace metal analysis [4]. Recently, the two H bridges have been substituted with metal complexes to obtain trinuclear compounds in order to investigate the magnetic interactions of the metal ionsr5].We have previously reported on the synthetic chemistry of MN4 core-containing complexes, namely phthalocyani n e~[~,~] and vic-dio~imates[*,~], with additional macrocyclic substituents. These macrocyclic vic-dioximes with four aza[lo1 or four this ["] groups are shown to be capable of forming trinuclear complexes.In the present work, our aim has been to undertake the synthesis of a vic-dioxime ligand carrying a 14-membered N202 macrocycle. The basicity of N donors in this macrocycle is rather low because of their position just near the oxime groups; i.e. their basicity is comparable with amides. However, three-nuclear complexes have been obtained by deprotonation of these NH groups. The synthesis of a pentanuclear complex has been also accomplished by insertion of the 1,lO-phenanthroline complex of Cu in the place of bridge hydrogen atoms. Results and Discussion 2,3-

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Synthesis and Complexation of a New 14‐Membered N₂O₂ Macrocycle with vic‐Dioxime Moieties

Hamuryudan

Bekâroĝlu

1994

Chem. Ber.

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Syntyhesis of 1,2,4,5‐Tetrazino[1,6‐a: 4,3‐a′]diquinoxaline

Koçak¹,

Berkâroǧlu²

1984

Helvetica Chimica Acta

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SummaryA new one-step synthesis of 2(1H)-quinoxalinone oxime (3) from (1,2-benzenediamine (1) and s-trans-chloroethanedial dioxime (2) is described. This oxime is converted into a new heterocyclic compound, 1,2,4,5,-tetrazino[ 1,6-a :4,3-af]diquinoxaline (4), by the template effect of Co(I1) and Ni(I1) ions.Introduction. ~ The aid of metal ions as templates to direct the steric course of condensations for heterocyclic compounds has been reported [ 1-31. A metal ion brings together the reactants by coordination and the reaction takes place in a series of stereochemically controlled steps. The template effect also enables the synthesis of some compounds which are not otherwise accessible. We have investigated the structures and transition metal complexes of diaminoglyoxime and its substituted derivatives [5-121. A completely conjugated 12-membered macrocycle, dibenzo[b,h]-1,4,7,1O-tetraazacyclododecyne, has been obtained by refluxing its octahydrodioxime derivative in dimethyl sulfoxide [ 131.A one-step preparation of 2(1H)-quinoxalinone oxime (3) is described, and a new heterocyclic ring system, 1,2,4,5-tetrazino[ 1,6-a :4,3-a']diquinoxaline, obtained a template reaction was introduced.

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Synthesis and Complexation of 1,2‐Bis[(monoaza[15]crown‐5)‐N‐yl]glyoxime. Crystal Structure of (1,2‐Bis[(monoaza[15]crown‐5)‐N‐yl]glyoximato)palladium(II)

Ahsen

Musluoğlu

Gürek

et al. 1990

Helvetica Chimica Acta

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Synthesis of Some Organometallic Compounds of 1,2-Acenaphthylenedione Dioxime and Comparision with 8₁₂Model Compounds

Cited by 25 publications

References 14 publications

Synthesis and Complexation of a New 14‐Membered N₂O₂ Macrocycle with vic‐Dioxime Moieties

Synthesis and Complexation of a New 14‐Membered N₂O₂ Macrocycle with vic‐Dioxime Moieties

Syntyhesis of 1,2,4,5‐Tetrazino[1,6‐a: 4,3‐a′]diquinoxaline

Synthesis and Complexation of 1,2‐Bis[(monoaza[15]crown‐5)‐N‐yl]glyoxime. Crystal Structure of (1,2‐Bis[(monoaza[15]crown‐5)‐N‐yl]glyoximato)palladium(II)

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Synthesis of Some Organometallic Compounds of 1,2-Acenaphthylenedione Dioxime and Comparision with 812Model Compounds

Cited by 25 publications

References 14 publications

Synthesis and Complexation of a New 14‐Membered N2O2 Macrocycle with vic‐Dioxime Moieties

Synthesis and Complexation of a New 14‐Membered N2O2 Macrocycle with vic‐Dioxime Moieties

Syntyhesis of 1,2,4,5‐Tetrazino[1,6‐a: 4,3‐a′]diquinoxaline

Synthesis and Complexation of 1,2‐Bis[(monoaza[15]crown‐5)‐N‐yl]glyoxime. Crystal Structure of (1,2‐Bis[(monoaza[15]crown‐5)‐N‐yl]glyoximato)palladium(II)

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Synthesis of Some Organometallic Compounds of 1,2-Acenaphthylenedione Dioxime and Comparision with 8₁₂Model Compounds

Synthesis and Complexation of a New 14‐Membered N₂O₂ Macrocycle with vic‐Dioxime Moieties

Synthesis and Complexation of a New 14‐Membered N₂O₂ Macrocycle with vic‐Dioxime Moieties