Radical fragmentation of omega-bromoalkyl cyclobutanones. A modular approach to eight-membered carbocycles.
[reaction: see text] An eight-membered ring was conveniently appended onto a cycloalkene carboxylate by employing a facile radical cyclization-fragmentation reaction of an omega-bromoalkyl spirocyclobutanone, which was readily accessible by the Kulinkovich cyclopropanation and subsequent electrophilic addition to a 3-bromoalkyl acetal.
Oh
Heong-Sub
HS
Department of Chemistry, University of Alabama, Tuscaloosa, Alabama 35487, USA.
Lee
Hyoung Ik
HI
Cha
Jin Kun
JK
D000478:Alkylation; D001966:Bromine / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry*; D008958:Models, Molecular
D002074:Butanones; D001966:Bromine