Investigation Into The Molecular Stability, Synthesis Mechanism, and Formation of Some Norcantharimide Derivatives Using AcCl or Ac2O: A Mechanism-Based Study

Authors : Aytekin KÖSE

Pages : 618-627

Doi:10.35414/akufemubid.1207578

View : 31 | Download : 22

Publication Date : 2023-06-28

Article Type : Research Paper

Abstract :The aim in this study was first to explain, in detail the conversion of diacetates over time into chlorinated monoacetates following ether cleavage with AcCl of norcantharimide derivatives with the help of the NMR technique and second, to verify this conversion theoretically and computationally. Ether cleavage reactions of N-methyl, N-benzyl, and N-acetoxyethyl-substituted norcantharimide derivatives were performed with Ac2O or AcCl in the presence of H2SO4, and the mechanisms of these reactions were elucidated in detail. According to the 1H NMR analyses of aliquots from the reactions with AcCl, trans-1,4-diacetates formed firstly. Upon the continuation of the reaction, trans-1,4-diacetates transformed into trans-1,2-chloroacetates via an SN2\` mechanism. Additionally, this explanation was further supported by the soft theoretical and physical calculations.
Keywords : Klorlanmış ürünler, , Norkantarimid, Aminler, SN2\` mekanizması