Co-host: The Chemical Society of Japan, The Society of Synthetic Organic Chemistry, Japan (Cooperation)
It has been known that alfa-haloketone shows remarkably enhanced reactivity in SN2 reaction. To clarify the origin of this effect, reaction pathways and transit states for the reactions of RCOCH2Cl (R=Me, Ar) and various nucleophiles (OH-, Cl-, CH3- and H2O) were calculated. It was found that the reaction pathway varied with a nucleophile, and that a strong nucleophile formed the carbonyl-carbon adduct, which then gave the substituted product through an intramolecular reaction. The experimental results for the reaction of PhCOCH2Cl and nucleophiles will also be discussed at the presentation.
