title: On the reactivity of tetrakis(trifluoromethyl)cyclopentadienone towards carbon-based Lewis bases.
abstract: The reactivitiy of tetrakis(trifluoromethyl)cyclopentadienone towards different C-based Lewis bases, such as N-heterocyclic carbenes (NHC), ylides and isonitriles, are reported. While sterically not hindered carbenes were found to yield kinetic adducts by regiospecific nucleophilic attack at the position adjacent to the carbonyl group of the ketone, bulkier nucleophiles afforded the thermodynamically more stable O-bridged zwitterions. Interestingly, isonitriles were found to dimerize and trimerize under the same reaction conditions, forming bicyclic products that evolve differently depending on the nature of the substituents.
authors.affiliation: Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2994.
authors.forename: Sigrid
authors.initials: S
authors.lastname: Holle
authors.forename: Daniel
authors.initials: D
authors.lastname: Escudero
authors.forename: Blanca
authors.initials: B
authors.lastname: Inés
authors.forename: Jörg
authors.initials: J
authors.lastname: Rust
authors.forename: Walter
authors.initials: W
authors.lastname: Thiel
authors.forename: Manuel
authors.initials: M
authors.lastname: Alcarazo
keywords: density functional calculations; isonitriles; organic Lewis acids; polyfluorinated ketones; zwitterions