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. ^ R. F. Feldkamp and B. F. Tullar (1963). "3-Methylthiophene". Organic Syntheses Collective Volume 4 34: 671. http://www.orgsyn.org/orgsyn/pdfs/CV4P0671.pdf. 
  2. ^ J. Volhard and H. Erdmann (1885). "Synthetische Darstellung von Thiophen (p )". Chemische Berichte 18 (1): 454–455. doi:10.1002/cber.18850180199.