Synthesis and polymerization of 2-vinylquinoline and 2-vinylnaphthalene with AlEt3-VCl3: Influence of pyridine as donor ligand

Conjugated 1,4-bis(nЈ-quinolyl)-1,3-butadiynes were obtained through the oxidative dimerization of the corresponding nЈ-ethynylquinolines catalyzed by cuprous chloride. Differential scanning calorimetry analysis of the 1,4-bis[nЈ-(quinolyl)]buta-1,3-diyne molecules produced evidence of a syn-anti rotational equilibrium around the 1,3-diyne axis and an irreversible transformation into a thermopolymer. The topooligomerization of 1,4-bis[3Ј-(quinolyl)]buta-1,3-diyne, which took place by irradiation with sunlight, was investigated with matrix-assisted laser desorption/ionization timeof-flight mass spectrometry. Accurate X-ray molecular structure and refinement analysis of 1,4-bis[3Ј-(quinolyl)]buta-1,3-diyne was conducted. The molecular crystalline packing consisted of parallel arrays of two groups of centrosymmetric molecules (antirotamer) in a herringbone assemblage in the solid state. The polymerization of 3-ethynylquinoline was carried out with the AlEt 3 /V(acac) 3 system to produce a mixture of 1,2,4-and 1,3,5-tris(3Ј-quinolyl)benzene cyclotrimers and a trans-cisoid polyene structure. RESULTS AND DISCUSSION Synthesis of n-Ethynylquinolines [2-Ethynylquinoline (1), 3-Ethynylquinoline (2), and 4-Ethynylquinoline (3)]1-3 were satisfactory obtained through the Sonogashira cross-coupling of an n-haloquinoline and 2-methyl-3-butyn-2-ol catalyzed by palladium. 11,12

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Thermal analysis of 1,4‐di[n′‐(quinolyl)]buta‐1,3‐diynes, structure, and topo‐oligomerization: Polymerization of 3‐ethynylquinoline with the triethyl aluminum/vanadium 2,4‐pentanedionate catalyst system

Rodriguez¹,

Lafuente²,

Rı́os³

2004

J. Polym. Sci. A Polym. Chem.

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Ziegler-Natta polymerization of 2-vinylpyridine with AlEt3-VCl3. Influence of nicotine as donor ligand

Fernández‐Sánchez

Muñoz

Rodriguez

1992

European Polymer Journal

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Synthesis and polymerization of 4-vinylquinoline and 4-vinylpyridine with AlEt3-VCl3: Influence of pyridine as donor ligand

Benito

Rodriguez

1994

European Polymer Journal

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Synthesis and polymerization of 2-vinylquinoline and 2-vinylnaphthalene with AlEt3-VCl3: Influence of pyridine as donor ligand

Cited by 6 publications

References 7 publications

Thermal analysis of 1,4‐di[n′‐(quinolyl)]buta‐1,3‐diynes, structure, and topo‐oligomerization: Polymerization of 3‐ethynylquinoline with the triethyl aluminum/vanadium 2,4‐pentanedionate catalyst system

Thermal analysis of 1,4‐di[n′‐(quinolyl)]buta‐1,3‐diynes, structure, and topo‐oligomerization: Polymerization of 3‐ethynylquinoline with the triethyl aluminum/vanadium 2,4‐pentanedionate catalyst system

Ziegler-Natta polymerization of 2-vinylpyridine with AlEt3-VCl3. Influence of nicotine as donor ligand

Synthesis and polymerization of 4-vinylquinoline and 4-vinylpyridine with AlEt3-VCl3: Influence of pyridine as donor ligand

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