New [4.4]Cyclophane diketals, monoketones, and diketones: Design, synthesis, and structural analysis

作者:Bogdan Niculina*; Grosu Ion; Condamine Eric; Toupet Loic; Ramondenc Yvan; Silaghi Dumitrescu Loan; Ple Gerard; Bogdan Elena
来源:European Journal of Organic Chemistry, 2007, (28): 4674-4687.
DOI:10.1002/ejoc.200700343

摘要

The synthesis of some new [4.4]cyclophane diketals, monoketones, and diketones in good yields is reported along with the unusually low reactivity towards hydrolysis of the spiro-1,3-dioxane rings connected to the cyclophane bridges. The structural analysis carried out by X-ray diffraction, NMR spectroscopy, and mass spectrometry shows significant intra- and intermolecular pi-pi and C-H-pi interactions. The rotation of the aromatic rings and the flipping of the bridges have been investigated by molecular modeling and variable-temperature NMR experiments.

  • 出版日期2007-10