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Skattebøl rearrangement



The Skattebøl rearrangement is an organic reaction for converting a geminal dihalo cyclopropane to an allene using an organolithium base. [1]. This rearrangement reaction is named after its discoverer, Lars Skattebøl. 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 [2] [3]:

References

  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. ^ ring system Chemistry of gem-dihalocyclopropanes—VI A novel synthesis of cyclopentadienes and fulvenes L. Skattebøl Tetrahedron Volume 23, Issue 3 , 1967, Pages 1107-1117 doi:10.1016/0040-4020(67)85060-9
  3. ^ Leo A. Paquette and Mark L. McLaughlin Organic Syntheses, CV 8, 223 Link
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Skattebøl_rearrangement". A list of authors is available in Wikipedia.
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