500573-18-2Relevant academic research and scientific papers
Divergent regioselectivity in the base-promoted reactions of cyclic eight-membered α-ketols with activated halides
Paquette, Leo A.,Vilotijevic, Ivan,Hilmey, David,Yang, Jiong
, p. 463 - 466 (2007/10/03)
(Matrix presented) 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 Δ5,6-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.
