Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions (Beilstein Journal of Organic Chemistry)

Abstract The selective ring-opening reaction of fluoroalkylidene-oxetanes was directed by the presence of the fluorine atom, enabling a two-step access to tetrasubstituted fluoroalkenes with excellent geometry control. Despite its small van der Waals radii electronic, rather than steric influences of the fluorine atom governed the ring-opening reaction with bromide ions, even in the presence of bulky substituents. Beilstein J. Org. Chem. 2020, 16, 1936–1946. doi:10.3762/bjoc.16.160