title: Divergent regioselectivity in the base-promoted reactions of cyclic eight-membered alpha-ketols with activated halides.
abstract: [reaction: see text] Deprotonation of 2-hydroxycyclooctanone followed by exposure to an allylic or benzylic halide proceeds very selectively to give the product of C-alkylation. The effect of Delta(5,6)-unsaturation is to promote instead the formation of the O-alkylated derivative. This crossover in kinetic preference is attributed to an inability of the olefinic system to attain a conformation conducive to proton abstraction at C-2.
authors.affiliation: Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA. paquette.1@osu.edu
authors.forename: Leo A
authors.initials: LA
authors.lastname: Paquette
authors.forename: Ivan
authors.initials: I
authors.lastname: Vilotijevic
authors.forename: David
authors.initials: D
authors.lastname: Hilmey
authors.forename: Jiong
authors.initials: J
authors.lastname: Yang