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Skattebøl rearrangement

From Wikipedia, the free encyclopedia
Organic reaction

TheSkattebøl rearrangement is anorganic reaction for converting ageminaldihalocyclopropane to anallene using anorganolithium base.[1][2] Thisrearrangement reaction is named after its discoverer,Lars Skattebøl, Professor emeritus at theUniversity of Oslo. It proceeds through acarbenereaction intermediate:

Skattebøl rearrangement
Skattebøl rearrangement

When the cyclopropane ring is fitted with a 2-vinyl group, acyclopentadiene is formed through a so-calledfoiled carbene intermediate.[3][4] This process is more generally known as avinylcyclopropane rearrangement.

Skattebøl rearrangement
Skattebøl rearrangement

The reaction is closely related to the earlier Doering-LaFlamme procedure (Doering–LaFlamme allene synthesis), in which agem-dibromocyclopropane is treated with analkali metal to form the same cyclopropylidene intermediate.[citation needed]

References

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  1. ^Moore, William R.; Ward, Harold R. (December 1962). "The Formation of Allenes from gem-Dihalocyclopropanes by Reaction with Alkyllithium Reagents 1,2".The Journal of Organic Chemistry.27 (12):4179–4181.doi:10.1021/jo01059a013.
  2. ^Skattebøl, Lars (September 1966). "Chemistry of gem-Dihalocyclopropanes. V. 1 Formation of Tricyclo[4.1.0.0 4,6 ]heptane and Derivatives".The Journal of Organic Chemistry.31 (9):2789–2794.doi:10.1021/jo01347a014.
  3. ^Skattebøl, Lars (January 1967). "Chemistry of gem-dihalocyclopropanes—VI".Tetrahedron.23 (3):1107–1117.doi:10.1016/0040-4020(67)85060-9.
  4. ^Paquette, Leo A.; McLaughlin, Mark L. (1960)."Cyclopentadiene annulation via the Skattebøl rearrangement: (1R)-9,9-Dimethyltricyclo-[6.1.1.02,6]deca-2,5-diene".Organic Syntheses.68: 220.doi:10.15227/orgsyn.068.0220;Collected Volumes, vol. 8, p. 223.
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