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Wagner-Jauregg reaction

 

 
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Wagner-Jauregg reaction
 
 
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The Wagner-Jauregg reaction is a classic 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....
 in organic chemistry
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, named after Theodor Wagner-Jauregg, describing the Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 of 2 equivalents of maleic anhydride
Maleic anhydride

Maleic anhydride is an organic compound with the formula C4H2O3. In its pure state it is a colourless or white solid with an acrid odour....
 with a 1,1-diarylethylene. After aromatization of the bis-adduct the ultimate reaction product is a naphthalene
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
 compound with one phenyl substituent.

The reaction is unusual in that the anhydride reacts with the related styrene
Styrene

Styrene, also known as vinyl benzene as well as many other names , is an organic compound with the chemical formula C6H5CH=CH2....
 to form a copolymer. The presence of the alpha-phenyl group activates the styryl group for a Diels–Alder reaction even at the expense of its aromaticity.

In one adaptation rearomatization is accomplished with elemental sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
 and decarboxylation
Decarboxylation

Decarboxylation is any chemical reaction in which a carboxyl group is split off from a compound as carbon dioxide ....
 with barium hydroxide
Barium hydroxide

Barium hydroxide is the chemical compound with the chemical formula Ba2. Also known as baryta, it is one of the principal compounds of barium....
 and copper
Copper

Copper is a chemical element with the symbol Cu and atomic number 29.It is a ductile metal with very high thermal and electrical conductivity....
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The Wagner-Jauregg reaction is a classic 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....
 in organic chemistry
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, named after Theodor Wagner-Jauregg, describing the Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 of 2 equivalents of maleic anhydride
Maleic anhydride

Maleic anhydride is an organic compound with the formula C4H2O3. In its pure state it is a colourless or white solid with an acrid odour....
 with a 1,1-diarylethylene. After aromatization of the bis-adduct the ultimate reaction product is a naphthalene
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
 compound with one phenyl substituent.

The reaction is unusual in that the anhydride reacts with the related styrene
Styrene

Styrene, also known as vinyl benzene as well as many other names , is an organic compound with the chemical formula C6H5CH=CH2....
 to form a copolymer. The presence of the alpha-phenyl group activates the styryl group for a Diels–Alder reaction even at the expense of its aromaticity.

In one adaptation rearomatization is accomplished with elemental sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
 and decarboxylation
Decarboxylation

Decarboxylation is any chemical reaction in which a carboxyl group is split off from a compound as carbon dioxide ....
 with barium hydroxide
Barium hydroxide

Barium hydroxide is the chemical compound with the chemical formula Ba2. Also known as baryta, it is one of the principal compounds of barium....
 and copper
Copper

Copper is a chemical element with the symbol Cu and atomic number 29.It is a ductile metal with very high thermal and electrical conductivity....
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