The Kowalski ester homologation 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, ...
for the
homologation
Homologation (Greek language, Greek ''homologeo'', ὁμολογέω, "to agree") is the granting of approval by an official authority. This may be a court of law, a government department, or an academic or professional body, any of which would n ...
of
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s.
This reaction was designed as a safer alternative to the
Arndt–Eistert synthesis, avoiding the need for
diazomethane
Diazomethane is an organic chemical compound with the formula CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow ga ...
. The Kowalski reaction is named after its inventor,
Conrad J. Kowalski
Conrad may refer to:
People
* Conrad (name)
* Saint Conrad (disambiguation)
Places
United States
* Conrad, Illinois, an unincorporated community
* Conrad, Iowa, a city
* Conrad, Montana, a city
* Conrad Glacier, Washington
Elsewher ...
.
Reaction mechanism
The mechanism is disputed.
Variations
By changing the
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
in the second step of the reaction, the Kowalski ester homologation can also be used for the preparation of
silyl
Silylation is the introduction of one or more (usually) substituted silyl groups (R3Si) to a molecule. Silylations are core methods for production of organosilicon chemistry. Silanization, while similar to silylation, usually refers to attachmen ...
ynol
In organic chemistry, alkynols (''hydroxyalkynes'') are organic compounds that contain both alkyne and alcohol functional groups. Thus, as structural features, they have a C≡C triple bond and a hydroxyl group. Some alkynols play a role as inte ...
ether
In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...
s.
See also
*
Curtius rearrangement
The Curtius rearrangement (or Curtius reaction or Curtius degradation), first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas. The isocyanate then undergoes attack by a ...
References
{{Reflist
Rearrangement reactions
Homologation reactions
Carbon-carbon bond forming reactions
Name reactions