title: Kinetic resolution in the [2+2] cycloaddition of ketenes: an experimental and theoretical study.
abstract: The kinetic resolution of Z and E olefins by [2+2] cycloaddition with ketenes allows the isolation of pure E olefin, as well as the synthesis of pure cis-cyclobutanones, starting from Z/E mixtures. A computational rationale for this kinetic difference is reported. The obtained difference of energy of activation matches with the experimental results.
authors: Université Joseph Fourier, CNRS, Département de Chimie Moléculaire, SERCO, UMR 5250, ICMG FR-2607, BP 53, 38041 Grenoble CEDEX 9 (France), Fax: (+33) 4-76-63-57-54.
authors: Pauline
authors: P
authors: Rullière
authors: Sébastien
authors: S
authors: Carret
authors: Anne
authors: A
authors: Milet
authors: Jean-François
authors: JF
authors: Poisson
mesh_terms: D000475:Alkenes / Q000737:chemistry* / Q000302:isolation & purification*; D002384:Catalysis; D061565:Cycloaddition Reaction; D005030:Ethylenes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D008962:Models, Theoretical; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D005030:Ethylenes; D007659:Ketones; C008223:ketene
keywords: cycloaddition; ketenes; kinetic resolution; olefins; stereochemistry