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Hunsdiecker reaction

 

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Hunsdiecker reaction



 
 
The Hunsdiecker reaction (also called the Borodin reaction after Alexander Borodin
Alexander Borodin

Alexander Porfiryevich Borodin was a Russian composer of Georgian people-Russian people parentage who made his living as a notable chemistry. He was a member of the group of composers called The Five , who were dedicated to producing a specifically Russian kind of art music....
) is the organic reaction
Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and organic redox reaction....
 of silver
Silver

Silver is a chemical element with the chemical symbol Ag and atomic number 47. A soft, white, lustrous transition metal, it has the highest electrical conductivity of any element and the highest thermal conductivity of any metal....
 salts of carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s with halogen
Halogen

|}The halogens or halogen elements are a chemical series of nonmetal chemical element from Periodic table group International Union of Pure and Applied Chemistry of the periodic table, comprising fluorine, F; chlorine, Cl; bromine, Br; iodine, I; and astatine, At....
s to give organic 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....
s. It is an example of a halogenation
Halogenation

Halogenation is a chemical reaction that incorporates a halogen atom into a molecule. More specific descriptions exist that specify the type of halogen: fluorination, chlorination, bromination, and iodination....
 reaction. The reaction is named after Heinz Hunsdiecker
Heinz Hunsdiecker

Heinz Hunsdiecker was a German chemist who together with his wife Cl?re Hunsdiecker improved a reaction of Alexander Borodin now known as the Hunsdiecker reaction....
 and Cläre Hunsdiecker.

Several reviews have been published.

Mercuric oxide will also effect this transformation.

reaction mechanism
Reaction mechanism

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....
 of the Hunsdiecker reaction is believed to involve organic radical
Radical (chemistry)

In chemistry, radicals are atoms, molecules or ions with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly chemical reaction, so radicals are likely to take part in chemical reactions....
 intermediates.






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Encyclopedia


The Hunsdiecker reaction (also called the Borodin reaction after Alexander Borodin
Alexander Borodin

Alexander Porfiryevich Borodin was a Russian composer of Georgian people-Russian people parentage who made his living as a notable chemistry. He was a member of the group of composers called The Five , who were dedicated to producing a specifically Russian kind of art music....
) is the organic reaction
Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and organic redox reaction....
 of silver
Silver

Silver is a chemical element with the chemical symbol Ag and atomic number 47. A soft, white, lustrous transition metal, it has the highest electrical conductivity of any element and the highest thermal conductivity of any metal....
 salts of carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s with halogen
Halogen

|}The halogens or halogen elements are a chemical series of nonmetal chemical element from Periodic table group International Union of Pure and Applied Chemistry of the periodic table, comprising fluorine, F; chlorine, Cl; bromine, Br; iodine, I; and astatine, At....
s to give organic 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....
s. It is an example of a halogenation
Halogenation

Halogenation is a chemical reaction that incorporates a halogen atom into a molecule. More specific descriptions exist that specify the type of halogen: fluorination, chlorination, bromination, and iodination....
 reaction. The reaction is named after Heinz Hunsdiecker
Heinz Hunsdiecker

Heinz Hunsdiecker was a German chemist who together with his wife Cl?re Hunsdiecker improved a reaction of Alexander Borodin now known as the Hunsdiecker reaction....
 and Cläre Hunsdiecker.

Hunsdiecker Reaction Scheme
Several reviews have been published.

Mercuric oxide will also effect this transformation.

Reaction mechanism

The reaction mechanism
Reaction mechanism

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....
 of the Hunsdiecker reaction is believed to involve organic radical
Radical (chemistry)

In chemistry, radicals are atoms, molecules or ions with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly chemical reaction, so radicals are likely to take part in chemical reactions....
 intermediates. The silver salt of the carboxylic acid 1 will quickly react with bromine to form intermediate 2. Formation of the diradical
Diradical

A diradical in organic chemistry is a molecule with two electrons occupying two degenerate molecular orbitals . They are known by their higher reactivities and shorter lifetimes....
 pair 3 allows for radical decarboxylation to form the diradical pair 4, which will quickly recombine to form the desired organic halide 5.


Variations


Simonini reaction

The reaction of silver salts of carboxylic acids with 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....
 is called the Simonini reaction , named after Angelo Simonini a student of Adolf Lieben
Adolf Lieben

Adolf Lieben was an Austrian Jewish chemist. He was born in Vienna as son of Ignatz Lieben. He studied at the University of Vienna, University of Heidelberg , and Paris, and subsequently held the positions of privat-docent at the University of Vienna , and professor in the universities of Palermo , Turin , and Prague ....
 at the University of Vienna
University of Vienna

The University of Vienna is a public university located in Vienna, Austria. Having opened in 1365, it is one of the oldest universities in Europe....
.


See also

  • Barton-McCombie deoxygenation
    Barton-McCombie deoxygenation

    The Barton-McCombie deoxygenation is an organic reaction in which an hydroxy functional group in an organic compound is replaced by a hydride to give an alkane ....
  • Kochi reaction
    Kochi reaction

    The Kochi reaction is an organic reaction for the decarboxylation of carboxylic acids to alkyl halides with lead tetraacetate and a lithium chloride or other lithium salts ....