Preparation of Tris(spiroorthocarbonate) Cyclophanes as Back to Back Ditopic Hosts

• Published in: Organic letters Vol. 15; no. 9; pp. 2164 - 2167
• Main Authors: Danjo, Hiroshi, Iwaso, Kazuhisa, Kawahata, Masatoshi, Ohara, Kazuaki, Miyazawa, Toshifumi, Yamaguchi, Kentaro
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 03.05.2013; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Crystallography, X-Ray; Ethers, Cyclic - chemical synthesis; Ethers, Cyclic - chemistry; Fullerenes; Kinetics; Magnetic Resonance Spectroscopy; Naphthalenes - chemical synthesis; Naphthalenes - chemistry; Physical Sciences; Piperidines - chemical synthesis; Piperidines - chemistry; Science & Technology; Spiro Compounds - chemical synthesis; Spiro Compounds - chemistry; DIMER; SUPRAMOLECULAR POLYMERS
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol4006882

Twin-bowl-shaped tris(spiroorthocarbonate) cyclophanes were designed and prepared as ditopic hosts for electrically neutral or electron-rich guests. Preparation of the desired cyclophanes was achieved by cyclotrimerization of 2,2′,3,3′-tetrahydroxy-1,1′-binaphthyl (THB) via the transesterification of tetraphenyl orthocarbonate or dichlorodiphenoxymethane. In those reactions, bis(spiroorthocarbonate) cyclophane containing two THB units was also formed as the kinetically favored product. The spiroorthocarbonate twin bowl exhibited ditopic molecular recognition toward fullerene C60 in the crystalline state.