The Volhard–Erdmann cyclization is an

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

of alkyl and aryl

thiophene Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reacti ...

s by cyclization of disodium

succinate Succinic acid () is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. In living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological roles as a metabolic intermediate being converted into Fuma ...

or other 1,4-difunctional compounds (γ-oxo acids, 1,4-diketones, chloroacetyl-substituted esters) with

phosphorus heptasulfide Phosphorus is a chemical element; it has symbol P and atomic number 15. All elemental forms of phosphorus are highly reactive and are therefore never found in nature. They can nevertheless be prepared artificially, the two most common allotrope ...

. The reaction is named after

Jacob Volhard Jacob Volhard (4 June 1834 – 14 January 1910) was the German chemist who discovered, together with his student Hugo Erdmann, the Volhard–Erdmann cyclization reaction. He was also responsible for the improvement of the Hell–Volhard–Zel ...

and

Hugo Erdmann Hugo Wilhelm Traugott Erdmann (8 May 1862 – 25 June 1910) was the German chemist who discovered, together with his doctoral advisor Jacob Volhard, the Volhard-Erdmann cyclization. In 1898 he was the first who coined the term ''noble gas'' (the ...

. An example is the synthesis of 3-methylthiophene starting from

itaconic acid Itaconic acid is an organic compound with the formula . With two carboxyl groups, it is classified as a dicarboxylic acid. It is a non-toxic white solid that is soluble in water and several organic solvents. It plays several roles in biology. ...

: :

References

{{DEFAULTSORT:Volhard-Erdmann cyclization Sulfur heterocycle forming reactions Name reactions