Methanofullerene Synthesis via Photogenerated Fullerene Radical Anion Intermediates

Sumino, Shuhei; Matsumoto, Fukashi; Iwai, Tomoaki; Ito, Takatoshi

doi:10.1021/acs.joc.1c00593

J. Org. Chem.

2021

DOI: 10.1021/acs.joc.1c00593

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Methanofullerene Synthesis via Photogenerated Fullerene Radical Anion Intermediates

Shuhei Sumino

Fukashi Matsumoto

Tomoaki Iwai

et al.

Abstract: This work describes the synthesis of PCBM ([6,6]phenyl-C 61 -butyric acid methyl ester) derivatives and other methanofullerene derivatives via generation of fullerene radical anions under photoirradiation and controlled by photoswitching, without preparation, a strong reducing agent, or precise control of the reaction conditions.

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Cited by 3 publications

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Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes

Chao,

Liu,

Zhang

et al. 2023

J. Org. Chem.

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An unexpected copper-mediated radical-induced ring-opening relay cascade carboannulation reaction of [60]fullerene with cyclobutanone oxime esters is presented for the preparation of various Cl-/Br-incorporated [60]fullerene-fused cyclopentanes. The unique relay cascade transformation uses inexpensive copper salts as promoters and halogen sources and features simple redox-neutral conditions and a broad substrate scope, providing a practical access to a class of novel five-membered carbocycle-fused fullerenes.

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Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes

Chao,

Liu,

Zhang

et al. 2023

J. Org. Chem.

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Chemodivergent Synthesis of Aza-Heterocycles with a Quarternary Carbon Center via [4 + 1] Annulation between Azoalkenes and α-Bromo Carbonyl Compounds

Zhang

Wang²,

Shu

et al. 2022

ACS Omega

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Information and thermodynamic entropies of regioisomeric fullerene cycloadducts C₆₀(CH₂)_n (n = 1, 2) and C₇₀CH₂

Tukhbatullina,

Turbin,

Sabirov

2024

EPJ Web Conf.

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The computations of the thermodynamic and information entropies of regioisomeric mono- and bisadducts of the C60 and C70 fullerenes with cyclopropane addends were performed with the density functional theory method. The regularities between the entropies and symmetry point groups of the molecules are discussed. For isomeric compounds, the calculated thermodynamic and information entropies vary in narrow ranges; the ranges for both entropies are narrower as compared with the ranges observed for these quantities of fullerenes themselves. The information entropy is recommended as a parameter for digital selecting the most and least symmetric structures.

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Methanofullerene Synthesis via Photogenerated Fullerene Radical Anion Intermediates

Cited by 3 publications

References 60 publications

Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes

Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes

Chemodivergent Synthesis of Aza-Heterocycles with a Quarternary Carbon Center via [4 + 1] Annulation between Azoalkenes and α-Bromo Carbonyl Compounds

Information and thermodynamic entropies of regioisomeric fullerene cycloadducts C₆₀(CH₂)_n (n = 1, 2) and C₇₀CH₂

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Product

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Methanofullerene Synthesis via Photogenerated Fullerene Radical Anion Intermediates

Cited by 3 publications

References 60 publications

Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes

Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes

Chemodivergent Synthesis of Aza-Heterocycles with a Quarternary Carbon Center via [4 + 1] Annulation between Azoalkenes and α-Bromo Carbonyl Compounds

Information and thermodynamic entropies of regioisomeric fullerene cycloadducts C60(CH2)n (n = 1, 2) and C70CH2

Contact Info

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Information and thermodynamic entropies of regioisomeric fullerene cycloadducts C₆₀(CH₂)_n (n = 1, 2) and C₇₀CH₂