Understanding the Mechanism of SN2′ vs. SN2 in Cascade Reaction of β‐Naphthol and Nitrostyrene Derived MBH Acetates

Abstract

AbstractThe reaction of β‐naphthol with nitrostyrene derived primary MBH acetates in presence of Cs2CO3 as base resulted in the formation of 3‐nitro‐4‐phenyl‐3,4‐dihydro‐2H‐naphthopyran as the major isomer via SN2′ process. Due to the bis‐electrophilic nature of MBH acetates, the minor product 3‐nitro‐2‐phenyl‐3,4‐dihydro‐2H‐naphthopyran was also obtained presumably due to SN2 process with ‐attack on MBH acetates. The state of the art density functional theory (DFT) calculations were carried out to account for these competitive pathways towards the formation of major and minor products.