Synthesis and structure of a chiral areno-bridged [2.4]metacyclophane |
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| Authors: | Thamina Akther MdMonarul Islam Taisuke Matsumoto Junji Tanaka Pierre Thuéry Carl Redshaw Takehiko Yamato |
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| Institution: | 1. Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga, 840-8502 Japan;2. Chemical Research Division, Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka, 1205, Bangladesh;3. Institute of Materials Chemistry and Engineering, Kyushu University, 6-1, Kasugakoen, Kasuga, 816-8580, Japan;4. NIMBE, CEA, CNRS, Université Paris-Saclay, CEA Saclay, 91191, Gif-sur-Yvette, France;5. Department of Chemistry, School of Mathematics and Physical Sciences, The University of Hull, Cottingham Road, Hull, Yorkshire, HU6 7RX, UK |
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| Abstract: | The reductive coupling reaction of 1,4-bis(3-acetyl-5-tert-butyl-2-methoxyphenyl)butane 3 was carried out using TiCl4-Zn in pyridine followed by a McMurry coupling reaction to afford the compounds anti and syn 1,2-dimethyl2.4]MCP-1-ene 4. Bromination of 4 with BTMA-Br3 in dry CH2Cl2 afforded the interesting compound 1,2-bis-(bromomethyl)-5,15-di-tert-butyl-8,18-dimethoxy2.4]MCP-1-ene 6 and consecutive debromination with Zn and AcOH in CH2Cl2 solution afforded the stable solid 5,15-di-tert-butyl-8,18-dimethoxy-1,2-dimethylene2.4]MCP 7 in 89% yield. Compound 7 was conveniently employed in a Diels–Alder reaction with dimethyl acetylenedicarboxylate (DMAD) to provide 2-(3′,6′-dihydrobenzo)-5,15-di-tert-butyl-8,18-dimethoxy2.4]MCP-4′,5′-dimethylcarboxylate 8 in good yield. Diels–Alder adduct 8 was converted into a novel and inherently chiral areno-bridged compound 2.4]MCP 9 by aromatization. The chirality of the two conformers was characterized by circular dichroism (CD) spectra of the separated enantiomer which are perfect mirror images of each other. |
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| Keywords: | Metacyclophane McMurry reaction Bromination Diels–Alder reaction Chirality |
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