Fullerene chemistry is a field of organic chemistry devoted to the chemical properties of fullerenes.. Research in this field is driven by the need to functionalize fullerenes and tune their properties.... is a fullerene
Fullerene
Fullerene are a family of carbon Allotropy, molecules composed entirely of carbon, in the form of a hollow sphere, ellipsoid, cylinder , or plane.... cyclopropanation reaction
Cyclopropane
Cyclopropane is a cycloalkane molecule with the molecular formula C3H6, consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms.... to a methanofullerene first discovered by C. Bingel in 1993 with the bromo derivative of diethyl malonate
Diethyl malonate
Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odor, and is used in perfumes.... in the presence of a base
Base (chemistry)
In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved.... such as sodium hydride
Sodium hydride
Sodium hydride is the chemical compound with the formula NaH. It is primarily used as a strong base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H- ions, in contrast to the more molecular hydrides such as borane, methane, ammonia and water.... or DBU
DBU (chemistry)
1,8-Diazabicyclo[5.4.0]undec-7-ene, or more commonly DBU, is a chemical compound and belongs to the class of amidine compounds. It is used in organic synthesis as a catalyst and complexing ligand and non-nucleophilic base.... . The preferred double bonds for this reaction on the fullerene surface are the shorter bonds at the junctions of two hexagons (6-6 bonds) and the driving force is relief of steric strain.
The reaction is of importance in the field of chemistry because it allows the introduction of useful extensions to the fullerene sphere.
Fullerene chemistry is a field of organic chemistry devoted to the chemical properties of fullerenes.. Research in this field is driven by the need to functionalize fullerenes and tune their properties.... is a fullerene
Fullerene
Fullerene are a family of carbon Allotropy, molecules composed entirely of carbon, in the form of a hollow sphere, ellipsoid, cylinder , or plane.... cyclopropanation reaction
Cyclopropane
Cyclopropane is a cycloalkane molecule with the molecular formula C3H6, consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms.... to a methanofullerene first discovered by C. Bingel in 1993 with the bromo derivative of diethyl malonate
Diethyl malonate
Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odor, and is used in perfumes.... in the presence of a base
Base (chemistry)
In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved.... such as sodium hydride
Sodium hydride
Sodium hydride is the chemical compound with the formula NaH. It is primarily used as a strong base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H- ions, in contrast to the more molecular hydrides such as borane, methane, ammonia and water.... or DBU
DBU (chemistry)
1,8-Diazabicyclo[5.4.0]undec-7-ene, or more commonly DBU, is a chemical compound and belongs to the class of amidine compounds. It is used in organic synthesis as a catalyst and complexing ligand and non-nucleophilic base.... . The preferred double bonds for this reaction on the fullerene surface are the shorter bonds at the junctions of two hexagons (6-6 bonds) and the driving force is relief of steric strain.
The reaction is of importance in the field of chemistry because it allows the introduction of useful extensions to the fullerene sphere. These extensions alter their properties for instance solubility and electrochemical behavior and therefore widen the range of potential technical applications.
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs .Although only the net chemical change is directly observation for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in a reaction mechanism.... for this reaction is as follows: a base
Base (chemistry)
In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved.... abstracts the acidic malonate proton generating a carbanion
Carbanion
A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons .... or enolate which reacts with the electron deficient fullerene double bond in a nucleophilic addition
Nucleophilic addition
In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a p bond is removed by the creation of two new covalent bonds by the addition of a nucleophile .... . This in turn generates a carbanion which displaces bromine in a nucleophilic aliphatic substitution in an intramolecular
Intramolecular
Intramolecular in chemistry describes a process or characteristic limited within the structure of a single molecule; a property or phenomenon limited to the extent of a single molecule.... ring cyclopropane
Cyclopropane
Cyclopropane is a cycloalkane molecule with the molecular formula C3H6, consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms.... ring closure.
Scope
The Bingel reaction is a popular method in fullerene chemistry. The malonate
Malonate
The malonate or propanedioate ion is carbonHydrogen222− . Malonate chemical compound include salts and esters of malonic acid, such as... (functionalized with the halide
Halide
A halide is a binary compound, of which one part is a halogen atom and the other part is an chemical element or radical that is less electronegative than the halogen, to make a fluoride, chloride, bromide, iodide, or astatide compound.... atom) is often obtained in situ
In situ
In situ is a Latin phrase meaning in the place. It is used in many different contexts.... in a mixture of base
Base (chemistry)
In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved.... and tetrachloromethane or iodine
Iodine
Iodine , is a chemical element that has the symbol I and atomic number 53. Naturally-occurring iodine is a single isotope with 74 neutrons.... . The reaction is also known to take place with the ester
Ester
An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water.... groups replaced by alkyne
Alkyne
Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e... groups in dialkynylmethanofullerenes.
An alternative to the Bingel reaction is a fullerene diazomethane
Diazomethane
Diazomethane is the chemical compound CH2N2. In the pure form at room temperature, it is a yellow gas, but it is almost universally used as a solution in diethyl ether.... reaction. N-(Diphenylmethylene)glycinate Esters in a Bingel reaction take a different conjugate course and react to a fullerene dihydropyrrole
Pyrrole
Pyrrole, or pyrrol, is a heterocyclic aromatic organic compound, a five-membered ring with the chemical formula carbon4hydrogen4nitrogenH.... .
