The Thorpe reaction is a

chemical reaction A chemical reaction is a process that leads to the chemistry, chemical transformation of one set of chemical substances to another. When chemical reactions occur, the atoms are rearranged and the reaction is accompanied by an Gibbs free energy, ...

described as a self-condensation of

aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...

s catalyzed by base to form

enamine An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates. The word "enamine" is derived from the affix ''en''-, used as the suffix of alkene, and the r ...

s. The reaction was discovered by Jocelyn Field Thorpe.

Thorpe–Ziegler reaction

The Thorpe–Ziegler reaction (named after Jocelyn Field Thorpe and

Karl Ziegler Karl Waldemar Ziegler (; 26 November 1898 – 12 August 1973) was a German chemist who won the Nobel Prize in Chemistry in 1963, with Giulio Natta, for work on polymers. The Nobel Committee recognized his "excellent work on organometallic comp ...

), or Ziegler method, is the intramolecular modification with a dinitrile as a reactant and a cyclic

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

as the final reaction product after acidic hydrolysis. The reaction is conceptually related to the

Dieckmann condensation The Dieckmann condensation is the Intramolecular reaction, intramolecular chemical reaction of ester, diesters with base to give β-keto esters. It is named after the German chemist Walter Dieckmann (1869–1925). The equivalent intermolecular rea ...

Thorpe Reaktion Mechanismus Schritt 1Version 5

References

{{Reflist

External links

* Thorpe-Ziegler reaction: ''4-Phosphorinanone, 1-phenyl-''

Organic Syntheses ''Organic Syntheses'' is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and expe ...

, Coll. Vol. 6, p. 932 (1988); Vol. 53, p. 98 (1973
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Carbon-carbon bond forming reactions Condensation reactions Name reactions