Volhard-Erdmann cyclization

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. [ cite journal
title = 3-Methylthiophene
author = R. F. Feldkamp and B. F. Tullar
volume = 34
pages = 671
year = 1963
journal = Organic Syntheses Collective Volume 4
url = http://www.orgsyn.org/orgsyn/pdfs/CV4P0671.pdf
]

An example is the synthesis of 3-methylthiophene starting from itaconic acid [ cite journal
title = Synthetische Darstellung von Thiophen (p )
author = J. Volhard and H. Erdmann
volume = 18
pages = 454–455
journal = Chemische Berichte
year = 1885
doi = 10.1002/cber.18850180199
] :

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References


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  • Jacob Volhard — Infobox Scientist name = Jacob Volhard image width = caption = Jacob Volhard birth date = birth date|1834|6|4 birth place = Darmstadt, Germany residence = Germany nationality = German death date = death date and age|1910|1|14|1834|6|4 death place …   Wikipedia

  • Hugo Erdmann — Infobox Scientist name = Hugo Erdmann image width = caption = Hugo Erdmann birth date = birth date|1862|5|8 birth place = Germany residence = Germany nationality = German death date = death date and age|1910|6|25|1862|5|8 death place = Müritzsee …   Wikipedia

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