Yang Mingyan, Wang Daoquan and Wang Mingan* Pages 1139 - 1147 ( 9 )
2-Phenylcyclododecanone and 2-cyclohexylcyclododecanone derivatives were synthesized and characterized by 1H NMR, 13C NMR, HR-ESI-MS and X-ray diffraction. Their preferred conformations were analyzed by the coupling constants in the 1H NMR spectra and X-ray diffraction, which showed the skeleton ring of these derivatives containing [3333]-2-one conformation, and the phenyl groups were located at the side-exo position of [3333]-2-one conformation due to the strong π-π repulsive interaction between the π- electron of benzene ring and π-electron of carbonyl group. The cyclohexyl groups were located at the corner-syn or the side-exo position of [3333]-2-one conformation depending on the hindrance of the other substituted groups. The π-π electron effect played a crucial role in efficiently controlling the preferred conformation of 2-aromatic cyclododecanone and the other 2-aromatic macrocyclic derivatives with the similar preferred square and rectangular conformations.
2-Phenylcyclododecanone, 2-cyclohexylcyclododecanone, [3333]-2-one conformation, π-π electron effect, conformation analysis, conformation control.
Department of Applied Chemistry, China Agricultural University, Beijing 100193, Department of Applied Chemistry, China Agricultural University, Beijing 100193, Department of Applied Chemistry, China Agricultural University, Beijing 100193