Md. Monarul Islam
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
Paris E. Georghiou
Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry
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.
|Journal Article Type||Article|
|Publication Date||Apr 1, 2019|
|Peer Reviewed||Peer Reviewed|
|APA6 Citation||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. https://doi.org/10.1002/slct.201900190|
|Keywords||Isomerization; Lewis acid; Metaparacyclophane; Strain; Transannular reaction; Trans-tert-butylation|
This file is under embargo until Apr 2, 2020 due to copyright reasons.
Contact C.Redshaw@hull.ac.uk to request a copy for personal use.
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