title: Exploiting a Difference in Leaving Group Ability: An Approach to β-Substituted Monofluoroalkenes Using gem-Chlorofluoropropenes.
abstract: The superior nucleofuge character of chlorine over fluorine was taken advantage of in the selective SN2' substitution reaction of gem-chlorofluoropropenes, allowing for the clean formation of β-substituted monofluoroalkenes under metal-free conditions. Numerous N-, S-, O-, and C-nucleophiles behaved nicely in this system. Further synthetic transformations of selected monofluoroalkenes were also accomplished.
authors.affiliation: CCVC, PROTEO, Département de chimie, Université Laval , 1045 Avenue de la Médecine, Québec, Québec, Canada G1V 0A6.
authors.forename: Jean-Denys
authors.initials: JD
authors.lastname: Hamel
authors.affiliation: CCVC, PROTEO, Département de chimie, Université Laval , 1045 Avenue de la Médecine, Québec, Québec, Canada G1V 0A6.
authors.forename: Mélissa
authors.initials: M
authors.lastname: Cloutier
authors.affiliation: CCVC, PROTEO, Département de chimie, Université Laval , 1045 Avenue de la Médecine, Québec, Québec, Canada G1V 0A6.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Paquin