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Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes: Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes

Islam, Md Monarul; Thuéry, Pierre; Akther, Thamina; Islam, Md. Monarul; Matsumoto, Taisuke; Tanaka, Junji; Thuery, Pierre; Redshaw, Carl; Yamato, Takehiko

Authors

Md Monarul Islam

Pierre Thuéry

Thamina Akther

Md. Monarul Islam

Taisuke Matsumoto

Junji Tanaka

Pierre Thuery

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Takehiko Yamato



Abstract

Bromination of 5,21-di-tert-butyl-8,24-dimethoxy-1,2-dimethyl[2.10]metacyclophan-1-ene (MCP-1-ene; 1) with benzyltrimethylammonium tribromide exclusively afforded 1,2-bis(bromomethyl)-5,21-di-tert-butyl-8,24-dimethoxy[2.10]MCP-1-ene (2). Debromination of 2 with Zn and AcOH in CH₂Cl solution at room temperature for 24 h produced dimethylene[2.10]MCP 7 in 92 % yield, which is a stable solid compound. Compound 7 was treated with dimethyl acetylenedicarboxylate (DMAD) to provide 1,2-(3′,6′-dihydrobenzo)-5,21-di-tert-butyl-8,24-dimethoxy[2.10]MCP-4′,5′-dimethylcarboxylate (8) in good yield. Diels–Alder adduct 8 was converted into a novel and inherently chiral areno-bridged dimethoxy[2.10]MCP-4′,5′-dimethylcarboxylate 9, possessing C₁ symmetry, by aromatization with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). A new type of N-phenyl-maleimide substituted 1,2-(3′,6′-dihydrobenzo)-5,21-di-tert-butyl-8,24-dimethoxy[2.10]MCP-4′,5′-N-phenylmaleimide 10 was also synthesized from 7 through treatment with N-phenylmaleimide in toluene at 110 °C followed by aromatization with DDQ. Single-crystal X-ray analysis of 9 revealed the formation of a syn-isomer.

Citation

Thuéry, P., Islam, M. M., Akther, T., Islam, M. M., Matsumoto, T., Tanaka, J., …Yamato, T. (2017). Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes: Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes. European Journal of Organic Chemistry, 2017(13), 1721-1726. https://doi.org/10.1002/ejoc.201601647

Acceptance Date Jan 23, 2017
Online Publication Date Apr 4, 2017
Publication Date Apr 3, 2017
Deposit Date May 9, 2017
Publicly Available Date Jan 24, 2018
Journal European journal of organic chemistry
Print ISSN 1434-193x
Electronic ISSN 1099-0690
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2017
Issue 13
Pages 1721-1726
DOI https://doi.org/10.1002/ejoc.201601647
Keywords 1,2-Dimethylene[2.10]metacyclophane; Chiral [10]Benzenometacyclophanes
Public URL https://hull-repository.worktribe.com/output/451187
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201601647/abstract;jsessionid=F778D40570FE9CE95602C913F33EA45D.f02t02
Copyright Statement ©2018 University of Hull
Additional Information Authors' accepted manuscript of article: Akther, T., Islam, Md. M., Matsumoto, T., Tanaka, J., Thuéry, P., Redshaw, C. and Yamato, T. (2017), Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes. Eur. J. Org. Chem., 2017: 1721–1726. doi:10.1002/ejoc.201601647

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