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Synthesis, structures and Lewis‐Acid‐Induced isomerization of 8‐Methoxy[2.2]metaparacyclophanes and a DFT study

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


Md. Monarul Islam

Xing Feng

Shofiur Rahman

Paris E. Georghiou

Taisuke Matsumoto

Junji Tanaka

Abdullah Alodhayb

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Professor Carl Redshaw
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Takehiko Yamato


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 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 1H 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.


Islam, M. M., Feng, X., Rahman, S., Georghiou, P. E., Matsumoto, T., Tanaka, J., …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.

Journal Article Type Article
Acceptance Date Mar 14, 2019
Online Publication Date Apr 1, 2019
Publication Date Apr 9, 2019
Deposit Date Apr 2, 2019
Publicly Available Date Apr 2, 2020
Journal ChemistrySelect
Electronic ISSN 2365-6549
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 4
Issue 13
Pages 3630-3635
Keywords Isomerization; Lewis acid; Metaparacyclophane; Strain; Transannular reaction; Trans-tert-butylation
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