Chemistry Department, Kuwait University , P.O. Box 5969, Safat 13060, Kuwait.
J Org Chem. 2017 Oct 20;82(20):10945-10952. doi: 10.1021/acs.joc.7b01837. Epub 2017 Oct 9.
We herein report the preparation of constitutional isomers of pentahydroxy-functionalized pillar[5]arenes via the deprotection of their benzylated derivatives by catalytic hydrogenation. The structures of the obtained isomers were then established using single crystal X-ray diffraction. We also found that the yield distribution of the different constitutional isomers was dependent on the nature of the substitution, as revealed by HPLC analysis of the crude mixture. Finally, further characterization of the separated constitutional isomers indicated that they possess different melting points, NMR spectra, crystal structures, and stacking patterns in the solid state.
我们在此报告通过催化氢化脱保护其苄基化衍生物来制备五羟官能化的[5]轮烷的顺反异构体。然后使用单晶 X 射线衍射确定了所得到的异构体的结构。我们还发现不同顺反异构体的产率分布取决于取代基的性质，这可以通过对粗混合物的 HPLC 分析来揭示。最后，对分离出的顺反异构体的进一步表征表明它们在固态下具有不同的熔点、NMR 谱、晶体结构和堆积模式。
