Skattebøl rearrangement
Encyclopedia
The Skattebøl rearrangement is an organic reaction
for converting a geminal
dihalo
cyclopropane
to an allene
using an organolithium base. This rearrangement reaction
is named after its discoverer, Lars Skattebøl, Professor emeritus at the University of Oslo
. It proceeds through a carbene
reaction intermediate
:
When the cyclopropane ring is fitted with a 2-vinyl
group, a cyclopentadiene
is formed through a so-called foiled carbene
intermediate :
Organic reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis,...
for converting a geminal
Geminal
In chemistry, the term geminal refers to the relationship between two functional groups that are attached to the same atom...
dihalo
Halogen
The halogens or halogen elements are a series of nonmetal elements from Group 17 IUPAC Style of the periodic table, comprising fluorine , chlorine , bromine , iodine , and astatine...
cyclopropane
Cyclopropane
Cyclopropane is a cycloalkane molecule with the molecular formula C3H6, consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms...
to an allene
Allene
An allene is a compound in which one carbon atom has double bonds with each of its two adjacent carbon centres. Allenes are classified as polyenes with cumulated dienes. The parent compound of allene is propadiene. Compounds with an allene-type structure but with more than three carbon atoms are...
using an organolithium base. This rearrangement reaction
Rearrangement reaction
A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another atom in the same molecule...
is named after its discoverer, Lars Skattebøl, Professor emeritus at the University of Oslo
University of Oslo
The University of Oslo , formerly The Royal Frederick University , is the oldest and largest university in Norway, situated in the Norwegian capital of Oslo. The university was founded in 1811 and was modelled after the recently established University of Berlin...
. It proceeds through a carbene
Carbene
In chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is RR'C:, but the carbon can instead be double-bonded to one group. The term "carbene" may also merely refer to the compound H2C:, also called...
reaction intermediate
Reaction intermediate
A reaction intermediate or an intermediate is a molecular entity that is formed from the reactants and reacts further to give the directly observed products of a chemical reaction. Most chemical reactions are stepwise, that is they take more than one elementary step to complete...
:
Vinyl
A vinyl compound is any organic compound that contains a vinyl group ,which are derivatives of ethene, CH2=CH2, with one hydrogen atom replaced with some other group...
group, a cyclopentadiene
Cyclopentadiene
Cyclopentadiene is an organic compound with the formula C5H6. This colorless liquid has a strong and unpleasant odor. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a Diels–Alder reaction...
is formed through a so-called foiled carbene
Foiled carbene
A foiled carbene in organic chemistry is a special type of stabilized carbene due to the proximity of a double bond. This type of reactive intermediate is implicated in certain organic reactions...
intermediate :