Volhard-Erdmann cyclization
Encyclopedia
The Volhard-Erdmann cyclization is an organic synthesis
of alkyl and aryl thiophene
s by cyclization of disodium succinate or other 1,4-difunctional compounds (γ-oxo acids, 1,4-diketones, chloroacetyl-substituted esters) with phosphorus heptasulfide
.The reaction is named after Jacob Volhard
and Hugo Erdmann
.
An example is the synthesis of 3-methylthiophene starting from itaconic acid
:
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
of alkyl and aryl thiophene
Thiophene
Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a flat five-membered ring, it is aromatic as indicated by its extensive substitution reactions. Related to thiophene are benzothiophene and dibenzothiophene, containing the thiophene ring fused with one and two benzene...
s by cyclization of disodium succinate or other 1,4-difunctional compounds (γ-oxo acids, 1,4-diketones, chloroacetyl-substituted esters) with phosphorus heptasulfide
Phosphorus sulfide
The Phosphorus sulfides comprise a family of inorganic compounds containing only phosphorus and sulfur. These compounds have the formula P4Sx where x is less than or equal to 10...
.The reaction is named after Jacob Volhard
Jacob Volhard
Jacob Volhard 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-Zelinsky halogenation....
and Hugo Erdmann
Hugo Erdmann
Hugo Wilhelm Traugott Erdmann was the German chemist who discovered, together with his doctoral advisor Jacob Volhard, the Volhard-Erdmann cyclization...
.
An example is the synthesis of 3-methylthiophene starting from itaconic acid
Itaconic acid
Itaconic acid, or methylenesuccinic acid, is an organic compound. Itaconic acid is a white crystalline powder. Itaconic acid is a naturally occurring compound, non-toxic, and readily biodegradable. The name itaconic was devised as an anagram of aconitic.Historically, itaconic acid was obtained by...
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