Synthesis, Structures and Conformational Studies of 1,2-Dimethyl[2.10]metacyclophan-1-enes - Archive ouverte HAL Access content directly
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Synthesis, Structures and Conformational Studies of 1,2-Dimethyl[2.10]metacyclophan-1-enes

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Abstract

A series of 1,2‐dimethyl[2.10]metacyclophan‐1‐enes (MCP‐1‐enes) containing different substituent groups has been synthesized to illustrate their conformational behavior. 4,22‐dimethoxy‐1,2‐dimethyl[2.10]MCP‐1‐ene 3 was synthesized by a Grignard coupling reaction, Friedel‐Crafts acylation reactions and McMurry coupling reaction from 1,10‐dibromodecane. The formation of 4,22‐dihydroxy‐1,2‐dimethyl[2.10]MCP‐1‐ene 4 was carried out by demethylation of compound 3 with boron tribromide at room temperature. The syn type conformation of 4 was characterized by X‐ray diffraction and was found to form both intramolecular and intermolecular hydrogen bonds between the two hydroxyl groups. From this reaction an interesting compound [10]tetrahydrobenzofuranophane 5 was afforded on prolonging the reaction time. 5,21‐diformyl‐4,22‐dihydroxy‐1,2‐dimethyl[2.10]MCP‐1‐ene 6 has been prepared from 4,22‐dihydroxy‐1,2‐dimethyl[2.10]MCP‐1‐ene 4 by using the Duff method in the presence of hexamethylenetetramine. Structural analysis by 1H NMR spectroscopy and X‐ray diffraction confirmed that both the solution and the crystalline state of compound 6 adopts an anti‐conformation which forms an intramolecular hydrogen bond between the formyl group and the hydroxyl group, which is an interesting finding for long carbon chain MCP compounds.

Dates and versions

cea-01758720 , version 1 (04-04-2018)

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Cite

Thamina Akther, Md Monarul Islam, Shofiur Rahman, Paris Georghiou, Taisuke Matsumoto, et al.. Synthesis, Structures and Conformational Studies of 1,2-Dimethyl[2.10]metacyclophan-1-enes. ChemistrySelect, 2016, 1 (13), pp.3594 - 3600. ⟨10.1002/slct.201600670⟩. ⟨cea-01758720⟩
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