Synthesis of substituted <i>N</i>-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory

Bastin, Loyd D.; Nigam, Manisha; Martinus, Sam; Maloney, James E.; Benyack, Landon L.

doi:10.1080/17518253.2019.1609596

Cited by 14 publications

(7 citation statements)

References 67 publications

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“…In that case, Lewis acid catalysts are essential, and hafnium(IV) chloride has shown the best performance. Moreover, higher endo/exo selectivity could be obtained when a catalytic amount of HfCl 4 was employed (Table , entries 5, 10). …”

Section: Reactions Of 25-dimethylfuran With Alkenesmentioning

confidence: 99%

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Kucherov

Romashov

Averochkin

et al. 2021

ACS Sustainable Chem. Eng.

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Rapid development in the area of cellulose biomass conversion to furanic platform chemicals has led to expectations of their valuable practical use. Impressive research progress in this direction has resulted in several achievements but at the same time identified a key challengethe necessity to produce aromatic compounds. In this perspective, we analyze the current stage of development of the furanics-tobenzene conversion process (F2B process) in connection with a bioderived route to aromatic compounds. Cycloaddition reactions between bioderived C 6 -furans as diene components and alkene/alkyne units are discussed in detail, followed by considering the subsequent aromatization reaction. Progress in the development of the F2B process and future challenges are outlined in this perspective. The key role of the F2B process in the overall biomass to aromatics transformation is discussed in view of the implementation of carbon neutral sustainable technologies in practice.

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Section: Reactions Of 25-dimethylfuran With Alkenesmentioning

confidence: 99%

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Kucherov

Romashov

Averochkin

et al. 2021

ACS Sustainable Chem. Eng.

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“…All acceptor maleimide-type ( A1–A4 ) as well as donor styrene-based D3 monomers were synthesized for the first time in relatively high yields. It should be noted that the approach for the synthesis of acceptor-type monomers developed in the present work is a simple and atom efficient synthetic method, which is suitable for fast access to a great variety of acceptor monomers.…”

Section: Resultsmentioning

confidence: 99%

Through-Space Charge-Transfer Thermally Activated Delayed Fluorescence Alternating Donor–Acceptor Copolymers for Nondoped Solution-Processable OLEDs

et al. 2023

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A series of donor−acceptor alternating copolymers with M n ≤ 12,000 g mol −1 and moderate polydispersity (Đ = 1.5− 2.5) were synthesized via RAFT copolymerization of styrene-based donor monomers and maleimide-type acceptor monomers in the presence of S-dodecyl-S′-(α,α′-dimethyl-α″-acetic acid)trithiocarbonate as a chain transfer agent. It was shown that synthesized alternating copolymers were characterized by high thermal stability (T d5 = 375−465 °C), and most of them exhibited exciplex emission via the through-space charge-transfer (TSCT) mechanism and displayed aggregation-induced emission. The color of the emission of synthesized copolymers largely depended on the nature of the acceptor monomer and could be changed from blue to orange depending on the copolymer structure. These copolymers in solid state demonstrated delayed fluorescence in the range between 0.35 and 6.2 μs and moderate photoluminescence quantum yield (2.12−6.32%) in air. Multicolor host-free solutionprocessable TADF OLEDs using synthesized alternating copolymers as emitters were fabricated, which showed good stability of electroluminescence spectra at different voltages. The highest external quantum efficiency of 7.84% was reached for the green emitting device.

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“…Bastin, Nigam, and co-workers reported a synthesis of substituted N -phenylmaleimides and demonstrated their use in a D–A reaction . Substituted N -phenylmaleimides are useful but expensive intermediates in organic synthesis.…”

Section: Diels–alder Reactionsmentioning

confidence: 95%

“…Bastin, Nigam, and co-workers reported a synthesis of substituted N-phenylmaleimides and demonstrated their use in a D−A reaction. 42 Substituted N-phenylmaleimides are useful but expensive intermediates in organic synthesis. The multistep synthesis experiment illustrates several green chemistry principles, such as a solvent-free reaction in a mortar or use of a green solvent, ethyl acetate, and use of a microwave as a heat source (Scheme 20).…”

Section: ■ Diels−alder Reactionsmentioning

confidence: 95%

Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

Mohan

Mejia

2020

J. Chem. Educ.

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Due to a growing awareness of environmental issues, green chemistry concepts are increasingly being incorporated into the undergraduate organic chemistry lecture and laboratory component. This minireview summarizes environmentally friendly organic chemistry experiments suitable for undergraduate laboratories. Whenever feasible, LD50 values for various chemicals are provided to allow readers to determine the suitability of an experiment for their curriculum based on the toxicity of reagents used.

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Synthesis of substituted N-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory

Abstract: Gainer (2019) Synthesis of substituted N-phenylmaleimides and use in a Diels-Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory,

Cited by 14 publications

References 67 publications

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Through-Space Charge-Transfer Thermally Activated Delayed Fluorescence Alternating Donor–Acceptor Copolymers for Nondoped Solution-Processable OLEDs

Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

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Synthesis of substituted N-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory

Abstract: Gainer (2019) Synthesis of substituted N-phenylmaleimides and use in a Diels-Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory,

Cited by 14 publications

References 67 publications

Biobased C6-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Biobased C6-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Through-Space Charge-Transfer Thermally Activated Delayed Fluorescence Alternating Donor–Acceptor Copolymers for Nondoped Solution-Processable OLEDs

Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

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Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks