Thorpe reaction
Encyclopedia
The Thorpe reaction is a chemical reaction
described as a self-condensation of aliphatic nitrile
s catalyzed by base
to form enamine
s. The reaction was discovered by Jocelyn Field Thorpe
.
and Karl Ziegler
), or Ziegler method, is the intramolecular
modification with a dinitrile as a reactant and a cyclic ketone
as the final reaction product after acidic hydrolysis. The reaction is conceptually related to the Dieckmann condensation
.
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
described as a self-condensation of aliphatic nitrile
Nitrile
A nitrile is any organic compound that has a -C≡N functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, one example being super glue .Inorganic compounds containing the -C≡N group are not called...
s catalyzed by base
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
to form enamine
Enamine
An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H2O.The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group...
s. The reaction was discovered by Jocelyn Field Thorpe
Jocelyn Field Thorpe
Sir Jocelyn Field Thorpe FRS was an English chemist who discovered the Thorpe reaction and the Thorpe-Ingold effect....
.
Thorpe–Ziegler reaction
The Thorpe–Ziegler reaction (named after Jocelyn Field ThorpeJocelyn Field Thorpe
Sir Jocelyn Field Thorpe FRS was an English chemist who discovered the Thorpe reaction and the Thorpe-Ingold effect....
and Karl Ziegler
Karl Ziegler
Karl Waldemar Ziegler 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 [which]...led to new polymerization reactions and ... paved the way for new and highly...
), or Ziegler method, is the intramolecular
Intramolecular
Intramolecular in chemistry describes a process or characteristic limited within the structure of a single molecule, a property or phenomenon limited to the extent of a single molecule.- Examples :...
modification with a dinitrile as a reactant and a cyclic ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
as the final reaction product after acidic hydrolysis. The reaction is conceptually related to the Dieckmann condensation
Dieckmann condensation
The Dieckmann condensation is the intramolecular chemical reaction of diesters with base to give β-ketoesters. It is named after the German chemist Walter Dieckmann . The equivalent intermolecular reaction is the Claisen condensation....
.
External links
- Thorpe-Ziegler reaction: 4-Phosphorinanone, 1-phenyl- Organic SynthesesOrganic SynthesesOrganic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. The journal is peer reviewed...
, Coll. Vol. 6, p.932 (1988); Vol. 53, p.98 (1973) Link