Polymerization of allene and its derivatives under the influence of bis-π-allylnickelbromide

Krentsel, B. A.; Mushina, E. A.; Khar’kova, E. M.; Shishkina, M. V.

doi:10.1016/0014-3057(75)90090-7

Cited by 12 publications

(4 citation statements)

References 16 publications

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“…In ref a, the polymerization of 1,2-butadiene by [(π-allyl)NiX] 2 (X = Cl, Br, and I, without PPh 3 ) were reported, where the ratio of the unsubstituted olefinic unit in the resulting polymer increased in the same order.…”

Section: Referencesmentioning

confidence: 98%

“…In ref a, the polymerization rate of 1,2-butadiene was also studied by [(π-allyl)NiX] 2 (X = Cl, Br, and I) in the absence of any ligands, where the rate is reported to increase in the order Cl < Br < I.…”

Section: Referencesmentioning

confidence: 99%

“…The allylnickel catalyst, [(allyl)Ni(X)L], possesses both anionic (X) and neutral (L) ligands, which may influence the polymerization behavior of alkoxyallenes. Although the effect of the ligand character on the polymerization rate and the polymer structure has been discussed in the coordination polymerization of alkylallene by π-allylnickel halides, the polymerization does not proceed sufficiently to give polymers in low yields . To clarify the effect of ligated systems on the polymerization behavior and to design the precise polymerization system for allene derivatives, we report the coordination polymerization of ( n -octyloxy)allene ( 2 ) by π-allylnickel catalysts having various anionic ligands ( 1a − 1e and 1f /Na 2 S 2 O 3 ) (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

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Living Coordination Polymerization of Alkoxyallenes by π-Allylnickel Catalyst. 2. Effect of Anionic Ligands on Polymerization Behavior and Polymer Structure

et al. 1998

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The coordination polymerization of (n-octyloxy)allene (2) was carried out by π-allylnickel catalysts possessing various carboxylate ligands (1a−1c). The electronic character of the carboxylate ligand strongly influences the polymerization. Electron-withdrawing groups provide a living system that produces polymers with well-defined molecular weights and narrow molecular weight distributions in high yields. Without electron-withdrawing substituents, the reaction produces oligomeric byproducts. The ratio of 1,2- to 2,3-polymerization unit in the polymer increased with the electron-withdrawing character of carboxylate ligands. π-Allylnickel catalysts bearing halide ligands (1d, 1e, and 1f/Na2S2O3) also gave polymers from 2 in high yields, in which the polymerization rate, the microstructure, and the molecular weight distributions (M w/M n) of polymers were dependent upon the specific halide. The catalyst with chloride (1d) afforded a polymer with narrow M w/M n (1.03), possessing the ratio of 1,2- to 2,3-polymerization unit of 6:94, whereas with iodide (1f/Na2S2O3), the polymerization took place much faster to give a polymer (1,2-:2,3-polymerization unit = 16:84) with a little broader M w/M n (1.10).

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Section: Referencesmentioning

confidence: 98%

Section: Referencesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Living Coordination Polymerization of Alkoxyallenes by π-Allylnickel Catalyst. 2. Effect of Anionic Ligands on Polymerization Behavior and Polymer Structure

et al. 1998

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“…The polymerization of allene (1,2‐propadiene) with Co 2 (CO) 8 was examined by Greenfield and coworkers . Otsuka et al and Krentsel et al have independently reported the polymerization of 1,2‐butadiene and 3‐methyl‐1,2‐butadiene by using π‐allylnickel catalysts . Thereafter, the living coordination polymerization of alkoxyallenes was developed by Endo and coworkers, in which the polymerization rate and polymer microstructure could be controlled by the structure of π‐allylnickel catalysts .…”

Section: Introductionmentioning

confidence: 99%

Cationic polymerization of n‐hexyloxyallene by using halogen‐bonding organocatalysts

Takagi

Okamura

2019

J. Polym. Sci. Part A: Polym. Chem.

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The cationic polymerization of n‐hexyloxyallene was investigated by using halogen‐bonding organocatalysts (Cat A–Cat D). Although the neutral catalyst Cat C showed a poor polymerization activity, iodine‐carrying bidentate cationic catalyst Cat A brought about the smooth polymerization giving rise to a polymer with Mn of 2710 under [Cat A]:[IBVE‐HCl]:[monomer] = 10:10:500 in mM concentrations. Judging from the color change of polymerization system and electrospray ionization mass spectra of recovered catalyst, the decomposition of organocatalyst was suggested. When α‐bromodiphenylmethane was used as an initiator, the relatively controlled polymerization proceeded at the low monomer conversion likely due to the weak halogen‐bonding interaction of Cat A with the bromide anion. On the other hand, bromine‐carrying bidentate catalyst Cat D gave low‐molecular‐weight polymers (Mn < 1550) to be less suitable for polymerization. From the 1H‐NMR spectrum, it was found that the 1,2‐polymerization unit and 2,3‐polymerization unit are included in 75:25. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2436–2441

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Polymerization of phenylallene, α‐methylphenylallene, and 1‐(1,2‐propadienyl)pyrrolidinone

Leland

Boucher

Anderson

1977

J. Polym. Sci. Polym. Chem. Ed.

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Polymerization of allene and its derivatives under the influence of bis-π-allylnickelbromide

Cited by 12 publications

References 16 publications

Living Coordination Polymerization of Alkoxyallenes by π-Allylnickel Catalyst. 2. Effect of Anionic Ligands on Polymerization Behavior and Polymer Structure

Living Coordination Polymerization of Alkoxyallenes by π-Allylnickel Catalyst. 2. Effect of Anionic Ligands on Polymerization Behavior and Polymer Structure

Cationic polymerization of n‐hexyloxyallene by using halogen‐bonding organocatalysts

Polymerization of phenylallene, α‐methylphenylallene, and 1‐(1,2‐propadienyl)pyrrolidinone

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