Synthesis of β‐Truxinate via [2+2] Cycloaddition of Methyl 4‐Nitrocinnamate: Kinetic Study of its Isomerization with DBU.

Abstract

AbstractThis work concerns the isomerization of the product obtained by dimerization of methyl 4‐nitrocinnamate. Subsequent isomerization was performed using 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) as a base to obtain the corresponding ζ‐ and δ‐truxinate derivatives. The process was monitored by 1H NMR spectroscopy in different deuterated solvents with a wide range of dielectric constants, acetonitrile‐d3, acetone‐d6, tetrahydrofuran‐d8, and benzene‐d6. Each solvent was found to have a distinct influence on the reaction's rate constant k, with acetone‐d6 yielding the highest ratio of ζ‐truxinate derivative. Kinetic analysis of the reaction provided valuable information about the mechanism involved in the isomerization process.