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Organocatalytic Dimerization of Ketoketenes

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journal contribution
posted on 20.02.2009, 00:00 by Ahmad A. Ibrahim, Gero D. Harzmann, Nessan J. Kerrigan
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 ≥16:1). Ring-opening reactions of the ketoketene dimers as well as preliminary studies toward the development of an asymmetric variant are also reported.