Volhard–Erdmann cyclization

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

  1. ↑ Feldkamp, R. F.; Tullar, B. F. (1954). "3-Methylthiophene" (PDF). Org. Synth. 34: 73.; Coll. Vol. 4, p. 671
  2. ↑ Volhard, J.; Erdmann, H. (1885). "Synthetische Darstellung von Thiophen". Chemische Berichte 18 (1): 454–455. doi:10.1002/cber.18850180199.
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