Skattebøl rearrangement

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The skattebøl rearrangement denotes an organic chemical reaction, the geminal cyclopropane - dihalides means of an organolithium -Base in an Allen transferred. The rearrangement reaction is named after its discoverer, the Norwegian chemist Lars Skattebøl (* 1927), professor emeritus at the University of Oslo . It runs over a carbene :

In the Skattebøl rearrangement, a carbene is formed as an intermediate.

If the cyclopropane ring bears a vinyl group in the 2-position , a cyclopentadiene is formed, since the carbene in the transition state is stabilized by the spatial proximity to a double bond.

2-Vinylcyclopropanes lead to cyclopentadienes in the Skattebøl rearrangement.

Such stabilized carbene in the English literature also foiled carbenes - to German as inhibited carbene - known as the Stabilization known pathways prevents the carbenes.

Individual evidence

  1. ↑ Chemistry of gem-Dihalocyclopropanes. V.1 Formation of Tricyclo [4.1.0.04,6] heptane and Derivatives Lars Skattebøl J. Org. Chem .; 1966 ; 31 (9); 2789-2794, doi : 10.1021 / jo01347a014 .
  2. ↑ Chemistry of gem-dihalocyclopropanes — VI A novel synthesis of cyclopentadienes and fulvenes L. Skattebøl Tetrahedron Volume 23, Issue 3, 1967 , pp. 1107-1117, doi : 10.1016 / 0040-4020 (67) 85060-9 .
  3. ↑ Leo A. Paquette and Mark L. McLaughlin: Cyclopentadiene Annulation via the Skattebøl Rearrangement: (1R) -9,9-Dimethyltricyclo- [6.1.1.0 2,6 ] deca-2,5- dienes Template: Linktext-Check / Escaped In: Organic Syntheses . 68, 1990, p. 220, doi : 10.15227 / orgsyn.068.0220 ; Coll. Vol. 8, 1993, p. 223 ( PDF ).