Nucleophilic cyclopropanation of [60]fullerene by the addition–elimination mechanism

Biglova, Yu. N.; Мустафин, А. Г.

doi:10.1039/c9ra04036f

Cited by 36 publications

(26 citation statements)

References 172 publications

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“…The results after removing the outliers by Smirnov-Grubbs test as a significance level of 0.05 along with other examples of Bingel reaction are presented in Figure 2 as an RTO model. [17][18][19] Regression coefficient and coefficient of determination shows high correlation between yield and reduced mass of raw materials. Third, KOtBu-promoted coupling reaction of phenol and C60 as shown in Scheme 4 was analyzed.…”

Section: Correlation Between Yield and Reduced Mass Of Raw Materials mentioning

confidence: 99%

“…In the case that the molecular weight of product exceeds around 1500, correlation is not revealed by the 1as shown in Figure 5 as a RTO model. 15,16,17,23,24 The author hypothesized that one of the causes is the degree of freedom of the molecule and attempted reaction examples used in this analysis are dendrimers, whose rotatable bonds are mainly derived from aliphatic carbon. Therefore, the author approximately calculated the reduced masses based on the molecular weight minus the mass of the methylene chain per a rotatable bond.…”

Section: Correlation Between Yield and Reduced Mass Of Raw Materials mentioning

confidence: 99%

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Correlation between Yield and Reduced Mass of Raw Materials in Reaction of Fullerene

Kawashima¹

2020

Preprint

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It turned out that the same regression equation between yield and reduced mass of raw materials holds in cycloaddition, Bingel reaction, and other reactions of fullerene. For the reactions, where the molecular weight of the product exceeds around 1500, reduced mass was obtained from molecular weight adjusted by number of rotatable bonds to show a similar correlation by the regression equation.

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Section: Correlation Between Yield and Reduced Mass Of Raw Materials mentioning

confidence: 99%

Section: Correlation Between Yield and Reduced Mass Of Raw Materials mentioning

confidence: 99%

Correlation between Yield and Reduced Mass of Raw Materials in Reaction of Fullerene

Kawashima¹

2020

Preprint

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“…The reaction scheme is reported in Figure 4 where the strong basic environment causes deprotonation of the 2-diethyl bromomalonate or methyl 2-chloroacetoacetate and a nucleophilic attack at the [6,6] position of the fullerene. The popularity of C 2019, 5, 84 9 of 45 this reaction stems from the possibility of easily modifying the original reaction to produce a vast class of different complexes [136].…”

Section: Fullerenesmentioning

confidence: 99%

“…Cycloaddition reaction of C 60 with 2-diethyl bromomalonate, methyl 2-chloro-acetoacetate. Reproduced with permission from[136].…”

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confidence: 99%

The Role of Functionalization in the Applications of Carbon Materials: An Overview

Speranza

2019

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The carbon-based materials (CbMs) refer to a class of substances in which the carbon atoms can assume different hybridization states (sp 1 , sp 2 , sp 3 ) leading to different allotropic structures -. In these substances, the carbon atoms can form robust covalent bonds with other carbon atoms or with a vast class of metallic and non-metallic elements, giving rise to an enormous number of compounds from small molecules to long chains to solids. This is one of the reasons why the carbon chemistry is at the basis of the organic chemistry and the biochemistry from which life on earth was born. In this context, the surface chemistry assumes a substantial role dictating the physical and chemical properties of the carbon-based materials. Different functionalities are obtained by bonding carbon atoms with heteroatoms (mainly oxygen, nitrogen, sulfur) determining a certain reactivity of the compound which otherwise is rather weak. This holds for classic materials such as the diamond, the graphite, the carbon black and the porous carbon but functionalization is widely applied also to the carbon nanostructures which came at play mainly in the last two decades. As a matter of fact, nowadays, in addition to fabrication of nano and porous structures, the functionalization of CbMs is at the basis of a number of applications as catalysis, energy conversion, sensing, biomedicine, adsorption etc. This work is dedicated to the modification of the surface chemistry reviewing the different approaches also considering the different macro and nano allotropic forms of carbon.C 2019, 5, 84 3 of 45 narrow graphite-like interconnected layers. This leads to a closed pore rigid structure that is chemically inert, hard but brittle [48][49][50].Due to the highly resistant, conductive, and inert network, glassy carbons are utilized in a series of rather different applications. They are utilized as electrodes in solid state batteries and in industrial harsh chemical processes where also high temperatures are involved such as crystallization of CaF2, CdS and ZnS. Glassy carbon can be utilized to manufacture high temperature furnace elements. Due to the chemical inertness, glassy carbons are utilized also in fabrication of protheses. Porous carbon and carbon black are much softer. Generally, in industrial applications important is the extension of the surface which is exposed to the external environment. The porous carbon is characterized by a high specific surface area enhancing the interaction with the external medium. Although it possesses a lower conductivity with respect to glassy carbon, the high porosity and the presence of active sites makes it a good material to fabricate electrodes for applications in electrochemistry [51][52][53] and bioelectrodes for sensing and stimulation [54,55].The same holds for the carbon black mainly utilized as additive in rubbers and polymers to improve their mechanical properties, or as a pigment [56] although new potentialities have been recently envisaged [57].Common to all the forms of carbon which are bri...

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“…With more than three decades of fullerene chemistry, modi-cation reactions have been developed which allow addition of a wide range of functional groups, thus transforming the all-carbon molecules into organic compounds with interesting properties, with applications ranging from organic photovoltaics to biomedicine. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Due to permanent curvature, the p-bonds of fullerenes are not conjugated. In contrast to planar aromatic compounds where a new substituent will affect the reactivity even at remote p-conjugated positions, fullerenes react at multiple positions leading to complex hardto-separate mixtures of mono-, bis-and more highly functionalized fullerenes.…”

Section: Introductionmentioning

confidence: 99%

Analytical and preparative separation and isolation of functionalized fullerenes by conventional HPLC stationary phases: method development and column screening

Dönmez

Grennberg

2020

RSC Adv.

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Nucleophilic cyclopropanation of [60]fullerene by the addition–elimination mechanism

Abstract: Generalized material on the synthesis of monosubstituted methanofullerenes C60, obtained by the addition–elimination mechanism.

Cited by 36 publications

References 172 publications

Correlation between Yield and Reduced Mass of Raw Materials in Reaction of Fullerene

Correlation between Yield and Reduced Mass of Raw Materials in Reaction of Fullerene

The Role of Functionalization in the Applications of Carbon Materials: An Overview

Analytical and preparative separation and isolation of functionalized fullerenes by conventional HPLC stationary phases: method development and column screening

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