The Thorpe reaction is a

chemical reaction A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the pos ...

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, like hexane, or ...

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...

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 th ...

s. The reaction was discovered by

Jocelyn Field Thorpe Sir Jocelyn Field Thorpe FRS (1 December 1872 – 10 June 1940) was a British chemist who made major contributions to organic chemistry, including the Thorpe-Ingold effect and three named reactions. Early life and education Thorpe was b ...

Thorpe–Ziegler reaction

The Thorpe–Ziegler reaction (named after

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 compounds ...

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

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

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

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

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 ex ...

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