Theoretical Study on the Mechanism of the Thermal Retro-Cycloaddition of Isoxazolinofullerenes

摘要: The retro-cycloaddition thermal reaction of isoxazolino[4,5:1,2][60]fullerenes to pristine fullerene seems be guided by the electronic nature substituted nitrile oxide 1,3-dipole in isoxazoline ring. Trapping experiments proved that mechanism occurs removal a process is favored presence big excess highly efficient dipolarophile such as maleic anhydride. Theoretical gas phase calculations carried out at B3LYP/6-31G(d) and M06-2X/6-31G(d) levels theory underpin experimental findings predict compound 1c, bearing p-(CH3)2N-Ph substituent on ring with remarkable conversion efficiency just 12 h, showed lowest activation energy. Solvent have predicted same behavior phase. Different approaches electrostatic natural population analysis Houk’s distortion/interaction model been applied understand how electronic...