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Synthesis and Conformational Studies of Novel Calixarene-Analogous Macrocyclic [3.1.1]Metacyclophanes

✍ Scribed by Yamato, Takehiko ;Doamekpor, Louis Korbla ;Tsuzuki, Hirohisa

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
791 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Hydroxy[3.1.1]metacyclophane 4c, which is regarded as an unsymmetric or uncomplete “homocalixarene” bearing a propane bridge, has been synthesized using Nafion‐H catalyzed cyclobenzylation. A novel “pendulum” type motion steered by intramolecular hydrogen bonding has been observed Demethylation of compound 4c with BBr~3~ in methylene dichloride was carried out at room temperature for 3 h to afford the dihydroxy[3.1.1]metacyclophane 4b in 74% yield along with the triol 4a in 25% yield. Triol 4a was tri‐O‐alkylated with methyl iodide in the presence of NaH to yield partial‐cone conformer 4d in quantitative yield. Similarly, a significant amount of partial‐cone conformer 5 results in the case of O‐alkylation of 4a with N,N‐diethylchloroacetamide. ^1^H‐NMR titration of partial‐cone amide 5 with NaSCN clearly demonstrates that a 1:1 complex is formed which is stable on the NMR time scale.

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