Synthesis, Structures and Lewis-Acid-Induced Isomerization of 8-Methoxy[2.2]metaparacyclophanes and a DFT Study

Md Monarul Islam, Xing Feng, Shofiur Rahman, Paris E. Georghiou, Taisuke Matsumoto, Junji Tanaka, Abdullah Alodhayb, Carl Redshaw, Takehiko Yamato

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2 Citations (Scopus)

Abstract

Methyl substituted 8-methoxy[2.2]MPCPs 8 a–b were obtained via thiacyclophane and its oxidized products. Lewis acid-catalyzed (AlCl 3 -MeNO 2 ) reactions of 5-tert-butyl-8-methoxy-12,13,15,16-tetramethyl[2.2]MPCP 8 b under various conditions led to transannular cyclization and 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 and pyrene derivatives 11 and 12. However,on prolonging the reaction time to 3 h for 8 b, the major product is 5-tert-butyl-8-hydroxy[2.2]MPCP 10. These reactions are strongly affected by the size and properties of the C-8 substitutents as well as the methyl substitutents on the para-linked benzene rings, which increase the strain in the molecules. The 1 H NMR spectra and X-ray crystallographic analysis of 8 b revealed that it adopts a syn-conformation both in solution and in the solid state.

Original languageEnglish
Pages (from-to)3630-3635
Number of pages6
JournalChemistrySelect
Volume4
Issue number13
DOIs
Publication statusPublished - Apr 9 2019

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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    Islam, M. M., Feng, X., Rahman, S., Georghiou, P. E., Matsumoto, T., Tanaka, J., Alodhayb, A., Redshaw, C., & Yamato, T. (2019). Synthesis, Structures and Lewis-Acid-Induced Isomerization of 8-Methoxy[2.2]metaparacyclophanes and a DFT Study. ChemistrySelect, 4(13), 3630-3635. https://doi.org/10.1002/slct.201900190