Skattebøl rearrangement

The Skattebøl rearrangement is an organic reaction for converting a geminal dihalo cyclopropane to an allene using an organolithium base.

[1][2] 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.

[3][4] This process is more generally known as a vinylcyclopropane rearrangement.

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 to form the same cyclopropylidene intermediate.