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Volumn 37, Issue 6, 2008, Pages 660-661

A bidirectional tunnel-like structure with a rigid, thick, and chiral aromatic macrocycle prepared by self-complementary 6,6′-substituted binaphthyl monomer

(6) Kumeda, Kazuhiro a Ono, Munetosi a Kawai, Atsushi a Oike, Hideaki a Noguchi, Keiichi a Yonezawa, Noriyuki a

a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 48249133643 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2008.660 Document Type: Article

Times cited : (3)

References (15)

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11
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- Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
- Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.

12
- 48249132553
- Typical procedure for the nucleophilic aromatic substitution cyclization is described in the fallowings: A solution of 6-(4-fluorobenzoyl)-6′- hydroxy-2,2′-dimethoxy-1,1′-binaphthyl (6, 0.2mmol) in 20 mL of DMF was added K2CO3 (0.3 mmol) and stirred in refluxing for 24 h. The mixture was poured into water (40 mL) and extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4. After removal of the solvent in vacuo, the reaction mixture was separated by PTLC (CHCl3) to afford dimer 7 (40, and timer 8 6
- 3) to afford dimer 7 (40%) and timer 8 (6%).

13
- 48249124338
- Dimer 7: 1HNMR (300MHz, CDCl3, δ 3.76 (3H, s, 3.85 (3H, s, 6.91 (1H, d, J, 9Hz, 6.96 (1H, d, J, 9Hz, 6.99-7.07 (2H, m, 7.42 (1H, dd, J, 9, 2Hz, 7.47 (1H, d, J, 9Hz, 7.53 (1H, d, J, 9 Hz, 7.60 (1H, d, J, 2Hz, 7.85 (2H, d, J, 9 Hz, 7.92 (1H, d, J, 9 Hz, 8.14 (1H, d, J, 9Hz, 8.56 (1H, d, J, 2 Hz, 13CNMR (75MHz, CDCl3, δ 56.6, 56.9, 114.5, 115.0, 115.1, 117.5, 118.1, 118.2, 121.9, 123.5, 125.9, 126.4, 127.3, 128.7, 129.0, 130.1, 130.5, 131.1, 131.4, 132.4, 132.9, 133.0, 135.6, 143.4, 149.8, 154.8, 193.8; IR (KBr, 1653, 1612, 1592, 1501, 1477, 1246cm-1; HRMS [M, H, m/z 865.2772 caled for C58H41O8, 865.2801
- 8, 865.2801).

14
- 48249103653
- Crystal data for cyclic dimer 7: C58H41O 8·3C4H8O2·CH 4O Mr, 1160.25, Orthorhombic, space group C2221, a, 13.1320(2, b, 17.5489(3, c, 26.8074(5) Å, V, 6177.82 Å3 Z, 4, Dcalcd, 1.2475(1) g cm -3, T, 155°C, R1, 0.09 (all data, wR 2, 0.26 all data, GOF, 1.074 for 5646 reflections and 375 parameters
- 2 = 0.26 (all data), GOF = 1.074 for 5646 reflections and 375 parameters.

15
- 0037178088
- K. Campbell, C. J. Kuehl, M. J. Ferguson, P. J. Stang, R. R. Tykwinski, J. Am. Chem. Soc. 2002, 124, 7266.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 7266
- Campbell, K.¹ Kuehl, C.J.² Ferguson, M.J.³ Stang, P.J.⁴ Tykwinski, R.R.⁵

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