Substituent effect on transition structure of Corey-Chaykovsky reaction: A semiempirical study

Abstract

Effect of various substituents on the conformation of transition structures of Corey-Chaykovsky reaction has been studied by semiempirical quantum mechanical method. It has been observed that steric effect and frontier interaction between substituent π electron and sulphur lone pair play a prominent role in determining the actual conformation of transition states. Based on the energy of the transition states, a probable explanation for showing high stereoselectivity of aromatic reagents involved in the above reaction has also been proposed.