Synthesis, Structures and Lewis-Acid-Induced Isomerization of 8-Methoxy[2.2]metaparacyclophanes and a DFT Study
作者： Md. Monarul Islam , Xing Feng , Shofiur Rahman , Paris E. Georghiou , Taisuke Matsumoto
关键词: Molecule 、 Isomerization 、 Solid-state 、 Chemistry 、 Strain (chemistry) 、 Medicinal chemistry 、 Benzene 、 Lewis acids and bases 、 Pyrene
摘要: Methyl substituted 8‐methoxy[2.2]MPCPs 8 a–b were obtained via thiacyclophane and its oxidized products. Lewis acid‐catalyzed (AlCl3‐MeNO2) reactions of 5‐tert‐butyl‐8‐methoxy‐12,13,15,16‐tetramethyl[2.2]MPCP 8 b under various conditions led to transannular cyclization isomerization reactions, affording the considerably less‐strained 5‐tert‐butyl‐8‐methoxy[2.2]MPCP 9, 5‐tert‐butyl‐8‐hydroxy‐14,16,17,18‐tetramethyl[2.2]metacyclophane 10 pyrene derivatives 11 12. However,on prolonging reaction time 3 h for 8 b, major product is 5‐tert‐butyl‐8‐hydroxy[2.2]MPCP 10. These are strongly affected by size properties C‐8 substitutents as well methyl on para‐linked benzene rings, which increase strain in molecules. The 1H NMR spectra X‐ray crystallographic analysis revealed that it adopts a syn‐conformation both solution solid state.
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