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Diazo refers to a type of organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 that has two linked nitrogen (azo) compounds. The general formula is R2C=N2. The simplest example of a diazo compound is 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....
. The electronic structure of diazo compounds involves a positive charge on the central nitrogen and negative charge distributed between the terminal nitrogen and the carbon. Some of the most stable diazo compounds are a-diazoketones and a-diazoesters since the negative charge is delocalized into the carbonyl.






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Diazo refers to a type of organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 that has two linked nitrogen (azo) compounds. The general formula is R2C=N2. The simplest example of a diazo compound is 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....
. The electronic structure of diazo compounds involves a positive charge on the central nitrogen and negative charge distributed between the terminal nitrogen and the carbon. Some of the most stable diazo compounds are a-diazoketones and a-diazoesters since the negative charge is delocalized into the carbonyl. In contrast, most alkyldiazo compounds are explosive.

Diazo compounds are used as precursors to carbene
Carbene

In chemistry, a carbene is a highly reactive organic molecule containing a carbon atom with six valence electrons and having the general formula: R1R2C: ....
s, which are generated by thermolysis or photolysis, for example in the Wolff rearrangement
Wolff rearrangement

The Wolff rearrangement is a rearrangement reaction converting a a-diazo-ketone into a ketene. This reaction was first reported by Ludwig Wolff in 1912....
. They are also used in transition metal
Transition metal

In chemistry, the term transition metal has two possible meanings:*It commonly refers to any element in the d-block of the periodic table, including the group 12 element elements zinc, cadmium and Mercury ....
-catalyzed cyclopropanation
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....
 reactions for example in a synthesis of tranylcypromine
Tranylcypromine

Tranylcypromine is a monoamine oxidase inhibitor used as an antidepressant medication. It is marketed by GlaxoSmithKline....
  in scheme 1 in which the sodium salt of benzaldehyde tosyl hydrazone is converted to a rhodium
Rhodium

Rhodium is a chemical element that is a rare, silvery-white, hard transition metal and a member of the platinum group. Rhodium is found in platinum ores and is used in alloys with platinum and as a catalyst....
 metal carbene through the diazo intermediate.

Diazo Cyclopropanation
An unusual biomolecule
Biomolecule

A biomolecule is any organic chemistry molecule that is produced by a living organism, including large polymeric molecules such as proteins, polysaccharides, and nucleic acids as well as small molecules such as primary metabolites, secondary metabolites, and natural products....
 sporting a diazo group was synthesized in 2006 with in its final stage the reaction of a carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
 group with the hydrazine
Hydrazine

Hydrazine is a chemical compound with the chemical formula N2H4. It is a colourless liquid with an ammonia-like odor and is derived from the same industrial chemistry processes that manufacture ammonia....
 1,2-bis(tert-butyldimethylsilyl)hydrazine to the hydrazone
Hydrazone

A hydrazone is a class of organic compounds with the structure R2C=NNR2. They are related to ketones and aldehydes by the replacement of the oxygen with the NNR2 functional group....
 followed by reaction with the periodinane
Periodinane

Periodinanes are chemical compounds containing hypervalent iodine. These iodine compounds are hypervalency because the iodine atom in it contains more than the 8 electrons in the valence shell required for the octet rule....
 difluoroiodobenzene to the diazo compound

Another commercially relevant diazocompound is Ethyl diazoacetate N2CHCOOEt.

A group of isomeric compounds with similar properties are the diazirines, where the carbon and two nitrogens are linked as a ring.

See also

  • Azo compound
    Azo compound

    Azo compounds are chemical compound bearing the functional group R-N=N-R', in which R and R' can be either aryl or alkyl. The N=N group is called an azo group, although the parent compound, HNNH, is called diimide....
  • Diazoalkane 1,3-dipolar cycloaddition
    Diazoalkane 1,3-dipolar cycloaddition

    The Diazoalkane 1,3-dipolar cycloaddition is a 1,3-dipolar cycloaddition between a 1,3-dipole diazo compounds and a dipolarophile. When the dipolarphile is an alkene, the reaction product is a pyrazoline....
  • Diazonium compound
    Diazonium compound

    Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group with the characteristic structure of R-N2+ X- where R can be any organic residue such alkyl or aryl and X is an inorganic or organic anion such as a halogen....
  • Reprography
    Reprography

    Reprography is the reproduction of graphics through mechanical or electrical means, such as photography or xerography. Reprography is commonly used in catalogs and archives, as well as in the architectural reprography....
  • Whiteprint
    Whiteprint

    Whiteprint is the commercial terminology to describe document reproduction using the diazo chemical process. It is also known as the blueline or blue-line process....