Skattebøl rearrangement

The Skattebøl rearrangement is an organic reaction for converting a geminal dihalo cyclopropane to an allene using an organolithium base ["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] . This rearrangement reaction is named after its discoverer, Lars Skattebøl, professor emeritus at the University of Oslo. 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 ["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 [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0223 Link] ] :

References