Structural properties of five- and six-layered [3.3]metacyclophanes

Masahiko Shibahara, Motonori Watanabe, Kenta Goto, Takaaki Miyazaki, Hua Zhang, Yuki Nakayama, Teruo Shinmyozu

Research output: Contribution to journalArticlepeer-review


We performed X-ray structural analyses of the five- and six-layered [3.3]metacyclophanes (MCPs) 1 and 2 and the six-layered [3.3]MCP tetraone 3. In the solid state, the MCP moieties of 1, 2, and 3 adopt different conformations from those of the free MCPs in solution. In the five-layered [3.3]MCP 1, all the [3.3]MCP moieties adopt anti (chair/boat) conformations. In the six-layered [3.3]MCP 2, two three-layered [3.3]MCPs are connected by a [3.3]MCP in the anti conformation with completely parallel benzene rings. In the six-layered [3.3]MCP tetraone 3, the outer [3.3]MCP moieties and diones adopt general syn and anti geometries, respectively. However, the inner [3.3]MCP moiety adopts an anti geometry. Based on density functional theory (DFT) calculations, the most stable conformers of 1, 2, and 3 are syn (chair/chair) in the [3.3]MCP moieties and anti (twist boat/twist boat) in the dione moieties.

Original languageEnglish
Pages (from-to)7089-7093
Number of pages5
JournalTetrahedron Letters
Issue number51
Publication statusPublished - Dec 17 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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