Volhard-Erdmann cyclization
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The Volhard-Erdmann cyclization is an organic synthesis of alkyl and aryl thiophenes 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.[1]
An example is the synthesis of 3-methylthiophene starting from itaconic acid [2]:
References
- ↑ R. F. Feldkamp and B. F. Tullar (1963). "3-Methylthiophene" (PDF). Organic Syntheses Collective Volume 4. 34: 671.
- ↑ J. Volhard and H. Erdmann (1885). "Synthetische Darstellung von Thiophen (p )". Chemische Berichte. 18: 454–455. doi:10.1002/cber.18850180199.