title: Organocatalytic dimerization of ketoketenes.
abstract: A general method for the catalytic dimerization of ketoketenes is described. Tri-n-butylphosphine was found to be the optimal organocatalyst for the racemic reaction. When lithium iodide was used as an additive, the reaction was rendered selective for dimer formation (dimer/trimer > or = 16:1). Ring-opening reactions of the ketoketene dimers as well as preliminary studies toward the development of an asymmetric variant are also reported.
authors.affiliation: Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, USA.
authors.forename: Ahmad A
authors.initials: AA
authors.lastname: Ibrahim
authors.forename: Gero D
authors.initials: GD
authors.lastname: Harzmann
authors.forename: Nessan J
authors.initials: NJ
authors.lastname: Kerrigan
mesh_terms: D002384:Catalysis; D019281:Dimerization; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D005030:Ethylenes; D007659:Ketones; C008223:ketene