TY - JOUR
T1 - Structural properties of five- and six-layered [3.3]metacyclophanes
AU - Shibahara, Masahiko
AU - Watanabe, Motonori
AU - Goto, Kenta
AU - Miyazaki, Takaaki
AU - Zhang, Hua
AU - Nakayama, Yuki
AU - Shinmyozu, Teruo
N1 - Funding Information:
This work was partially supported by a Grant-in-Aid for Science Research ( C 25410050 ) from the Japan Society for the Promotion of Science (JSPS), Japan, and was performed under the Cooperative Research Program of the Network Joint Research Center for Materials and Devices (IMCE, Kyushu University). The computations were performed at the computer facilities of the Research Institute for Information Technology, Kyushu University. M.W. thanks the World Premier International Research Center Initiative (WPI), Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), Japan.
Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.
PY - 2014/12/17
Y1 - 2014/12/17
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tetlet.2014.10.151
DO - 10.1016/j.tetlet.2014.10.151
M3 - Article
AN - SCOPUS:84911933918
SN - 0040-4039
VL - 55
SP - 7089
EP - 7093
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 51
ER -