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:
![Skattebøl rearrangement](https://upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Skatteb%C3%B8l_rearrangement_general.png/500px-Skatteb%C3%B8l_rearrangement_general.png)
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.
![Skattebøl rearrangement](https://upload.wikimedia.org/wikipedia/commons/thumb/5/53/Skatteb%C3%B8l_rearrangement.png/500px-Skatteb%C3%B8l_rearrangement.png)
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.
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