title: Computational study of productive and non-productive cycles in fluoroalkene metathesis.
abstract: A detailed DFT study of the mechanism of metathesis of fluoroethene, 1-fluoroethene, 1,1-difluoroethene, cis- and trans-1,2-difluoroethene, tetrafluoroethene and chlorotrifluoroethene catalysed with the Hoveyda-Grubbs 2(nd) generation catalyst was performed. It revealed that a successful metathesis of hydrofluoroethenes is hampered by a high preference for a non-productive catalytic cycle proceeding through a ruthenacyclobutane intermediate bearing fluorines in positions 2 and 4. Moreover, the calculations showed that the cross-metathesis of perfluoro- or perhaloalkenes should be a feasible process and that the metathesis is not very sensitive to stereochemical issues.
authors.affiliation: Department of Organic Chemistry, University of Chemistry and Technology, Technická 5, 166 28 Prague 6, Czech Republic.
authors.forename: Markéta
authors.initials: M
authors.lastname: Rybáčková
authors.affiliation: Department of Organic Chemistry, University of Chemistry and Technology, Technická 5, 166 28 Prague 6, Czech Republic.
authors.forename: Jan
authors.initials: J
authors.lastname: Hošek
authors.affiliation: Department of Organic Chemistry, University of Chemistry and Technology, Technická 5, 166 28 Prague 6, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Šimůnek
authors.affiliation: Department of Organic Chemistry, University of Chemistry and Technology, Technická 5, 166 28 Prague 6, Czech Republic.
authors.forename: Viola
authors.initials: V
authors.lastname: Kolaříková
authors.affiliation: Department of Organic Chemistry, University of Chemistry and Technology, Technická 5, 166 28 Prague 6, Czech Republic.
authors.forename: Jaroslav
authors.initials: J
authors.lastname: Kvíčala
keywords: DFT; alkene metathesis; computation; fluoroalkene; mechanism; non-productive cycle; productive cycle