Niobium(V) Chloride as Catalyst in Diels-Alder Reaction of Furan Ring

Santos, Deborah A. dos; Rodrigues, Ludmila R.; Arpini, Bruno H.; Lacerda, Valdemar; Greco, Sandro J.; Santos, Reginaldo Bezerra dos; Neto, Álvaro Cunha; Romão, Wanderson; Castro, Eustáquio Vinícius Ribeiro de

doi:10.5935/0103-5053.20140052

Cited by 2 publications

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“…It has been reported that AN can react with furan via the Diels–Alder reaction. [ 52–54 ] The furan/acrylonitrile adduct (FAN) (Figure S1, Supporting Information) was initially produced via the Diels‐Alder (D–A) reaction. The kinetics of the retro Diels‐Alder reaction (rD–A) of FAN indicated a low reaction rate (Figure S2, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…It is noted that the AN as a dienophile can also react with diene like furan, via the Diels‐Alder reaction (D–A). [ 52,53 ] Therefore, we proposed that the furan/AN adduct could be used as the latent monomer of AN, which enabled the sequence control via the latent monomer strategy. Herein, the 2,5‐dimethylfuran/acrylonitrile adduct was applied as the latent acrylonitrile toward the production of sequence‐controlled AN‐based polymers ( Scheme ).…”

Section: Introductionmentioning

confidence: 99%

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2,5‐Dimethylfuran/Acrylonitrile as Latent Monomer for Sequence‐Controlled Copolymer and Sequence‐Dependent Thermo‐Responsivity

Gao

Zhang

Jia

et al. 2021

Macromol. Rapid Commun.

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Sequence control has attracted increasing attention for its ability of regulating polymer property and performance. Herein, the sequence‐controlled polymer containing acrylonitrile (AN) is achieved by using 2,5‐dimethylfuran/acrylonitrile adduct as a latent monomer. The temperature‐dependent retro Diels–Alder reaction is engaged in controlling the release of AN during RAFT polymerization, that is, regulating the instant AN concentration via a non‐invasive and in situ manner. Such control over the instant AN concentration and particularly the molar ratio of comonomer pair leads to the simultaneous change of monomer units in “living” polymeric chain, thus resulting in the sequence–controlled polymeric structures. By delicately manipulating the polymerization temperature, diverse sequence‐on‐demand structures of AN‐containing copolymers, such as poly(AN/methyl methacrylate), poly(AN/styrene), poly(AN/butyl acrylate), poly(AN/N,N‐dimethylacrylamide), and poly(AN/N‐isopropylacrylamide) are created. Meanwhile, this study presents an initial attempt in tuning the thermal responsivity of poly(AN/N‐isopropylacrylamide), which is closely correlated to the sequence of polymer structure. More importantly, the polymer with averagely distributed AN units results in the higher thermal sensitivity. Therefore, the synthetic strategy proposed in this work offers a promising platform for accessing the sequence‐controlled copolymers containing AN structures, thus expanding the investigation on the relationship between the polymer structures and correlated properties.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

2,5‐Dimethylfuran/Acrylonitrile as Latent Monomer for Sequence‐Controlled Copolymer and Sequence‐Dependent Thermo‐Responsivity

Gao

Zhang

Jia

et al. 2021

Macromol. Rapid Commun.

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“…In addition, its aromatic stability enables the easy retro-cycloaddition pathway. Lacerda's group found that a catalytic amount of Nb(V) chloride is highly efficient for the cycloaddition of furan with methyl acrylate 83, yielding quantitatively the adduct (84) with slight endo selectivity (Scheme 23) [50].…”

Section: Niobium (Nb)mentioning

confidence: 99%

Metal Promoted Diels-Alder Reactions

Gallier¹

2016

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Niobium(V) Chloride as Catalyst in Diels-Alder Reaction of Furan Ring

Cited by 2 publications

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2,5‐Dimethylfuran/Acrylonitrile as Latent Monomer for Sequence‐Controlled Copolymer and Sequence‐Dependent Thermo‐Responsivity

2,5‐Dimethylfuran/Acrylonitrile as Latent Monomer for Sequence‐Controlled Copolymer and Sequence‐Dependent Thermo‐Responsivity

Metal Promoted Diels-Alder Reactions

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