Paal-Knorr synthesis

Paal-Knorr synthesis

The Paal-Knorr synthesis is a reaction where 1,4-diketones are converted to either furans, thiophenes or pyrroles. The reaction is named after Carl Paal and Ludwig Knorr [cite journal
title = Synthese von Thiophen- und Pyrrolderivaten
author = Carl Paal
journal = Berichte der deutschen chemischen Gesellschaft
volume = 18
issue = 1
pages = 367–371
year = 1885
url =
doi = 10.1002/cber.18850180175
] [cite journal
title = Einwirkung des Diacetbernsteinsäureesters auf Ammoniak und primäre Aminbasen
author = Ludwig Knorr.
journal = Berichte der deutschen chemischen Gesellschaft
volume = 18
issue = 1
pages = 299–311
year = 1885
url =
doi = 10.1002/cber.18850180154
] [cite journal
url = http://www.chempensoftware.com/reactions/RXN282.htm
title = Paal-Knorr Pyrrole Synthesis
] .

The furan synthesis requires an acid catalyst ["Heterocyclic chemistry" T.L. Gilchrist ISBN 0-582-01421-2] :

:

In the pyrrole synthesis a tertiary amine participates:

:

and in that of thiophene for instance the compound phosphorus pentasulfide: :

References


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