The Skattebøl rearrangement is an

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, mechanistic organ ...

for converting a

geminal In chemistry, the descriptor geminal () refers to the relationship between two atoms or functional groups that are attached to the same atom. A geminal diol, for example, is a diol (a molecule that has two alcohol functional groups) attached to ...

dihalo

cyclopropane Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene groups (CH2) linked to each other to form a triangular ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane ...

to an

allene In organic chemistry, allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon atoms (, where R is hydrogen, H or some organyl group). Allenes are classified as diene#Classes, cumulated dienes ...

using an

organolithium In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...

base. This

rearrangement reaction In organic chemistry, 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 at ...

is named after its discoverer,

Lars Skattebøl Lars Skattebøl FRSC (born 16 July 1927) is a Norwegian scientist and professor emeritus at the University of Oslo. The Skattebøl rearrangement, a chemical reaction, was named after his discovery. He was born in Bærum. Skattebøl received his ...

, Professor emeritus at the

University of Oslo The University of Oslo (; ) is a public university, public research university located in Oslo, Norway. It is the List of oldest universities in continuous operation#Europe, oldest university in Norway. Originally named the Royal Frederick Univ ...

. It proceeds through a

carbene In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a Valence (chemistry), valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. Th ...

reaction intermediate In chemistry, a reaction intermediate, or intermediate, is a molecular entity arising within the sequence of a stepwise chemical reaction. It is formed as the reaction product of an elementary step, from the reactants and/or preceding interme ...

: When the cyclopropane ring is fitted with a 2-

vinyl group In organic chemistry, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a functional group with the formula . It is the ethylene (IUPAC name: ethene) molecule () with one fewer hydrogen atom. The name is also used for any compound contai ...

, a

cyclopentadiene Cyclopentadiene is an organic compound with the chemical formula, formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−. This colorless liquid has a strong and unpleasant odor. At room temperature, ...

is formed through a so-called

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. The positive interaction between carbene and double ...

intermediate. This process is more generally known as a

vinylcyclopropane rearrangement The vinylcyclopropane rearrangement or vinylcyclopropane-cyclopentene rearrangement is a ring expansion reaction, converting a vinyl-substituted cyclopropane ring into a cyclopentene ring. Cyclopropyl groups adjacent to vinyl groups can undergo ri ...

. The reaction is closely related to the earlier Doering-LaFlamme procedure ( Doering–LaFlamme allene synthesis), in which a ''gem-''dibromocyclopropane is treated with an

alkali metal The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K),The symbols Na and K for sodium and potassium are derived from their Latin names, ''natrium'' and ''kalium''; these are still the origins of the names ...

to form the same cyclopropylidene intermediate.

References

{{DEFAULTSORT:Skattebol rearrangement Rearrangement reactions Name reactions