Skattebøl rearrangement
From Wikipedia, the free encyclopedia
The Skattebøl rearrangement is an organic reaction converting a geminal dihalo cyclopropane to an allene with an organolithium base [1]:
This rearrangement reaction is named after its discoverer. The reaction proceeds through a carbene reactive 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]:
[edit] References
- ^ Chemistry of gem-Dihalocyclopropanes. V.1 Formation of Tricyclo[4.1.0.04,6]heptane and Derivatives J. Org. Chem.; 1966; 31(9); 2789-2794 DOI:10.1021/jo01347a014 10.1021/jo01347a014
- ^ 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
- ^ Leo A. Paquette and Mark L. McLaughlin Organic Syntheses, CV 8, 223 Link
