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Tuesday, 22 March 2016

p-(4-Cyclohexylphenyl)aniline

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p-(4-Cyclohexylphenyl)aniline (2c)

A reported procedure was generally followed to synthesize 2c. A mixture of 4-bromocyclohexylbiphenyl (12) (1.9 g, 60 mmol, 1.0 equiv), Cu2O (0.086 g, 0.60 mmol, 0.010 equiv), aqueous ammonia (30% solution, 8.4 mL, 120 mmol, 20 equiv), and NMP (8.4 mL, 120 mmol, 20 equiv) was stirred at 100 °C in a sealed tube under Ar atmosphere. After 39 h, the solution was cooled at room temperature, quenched with water, and extracted with CH2Cl2.

The combined organic layer was washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash silica gel column chromatography using hexane/ethyl acetate (10/1 (v/v)) to afford 2c (0.91 g, 36 mmol, 60%) as a white powder. Mp: 101.0–101.5 °C (lit. mp 102 °C).........Basford, F. R. J. Chem. Soc. 1937, 14401443, DOI: 10.1039/jr9370001440
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1H NMR (500 MHz, CDCl3) δ: 7.47 (d, J = 8.0 Hz, 2H), 7.41 (d, J = 8.0 Hz, 2H), 7.25 (d, J = 8.0 Hz, 2H), 6.75 (d, J = 8.0 Hz, 2H), 3.67 (br s, 2H), 2.53 (t, J = 10.0 Hz, 1H), 1.96–1.72 (m, 5H), 1.51–1.22 (m, 5H).

13C NMR (125 MHz, CDCl3) δ: 146.3, 145.7, 138.8, 131.8, 128.0, 127.3, 126.4, 115.6, 44.3, 34.7, 27.1, 26.4.

IR (ATR): 3397, 3386, 3324, 3311, 3212, 3026, 2920, 2846, 1604, 1495, 1445, 1265, 1178, 1138, 1000, 807, 692, 515, 474 cm–1.


Anal. Calcd for C18H21N: C, 86.01; H, 8.42; N, 5.57. Found: C, 86.00; H, 8.47; N, 5.58.

11H NMR BELOW
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  13C NMR


 1H NMR PREDICT


 13C NMR PREDICT

 

Synthesis and Shuttling Behavior of [2]Rotaxanes with a Pyrrole Moiety

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601,Japan
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan
§ Research Center for Medical and Dental Sciences, Tokyo Medical and Dental University, 1-5-45 Yushima, Bunkyo-ku, Tokyo 113-8510, Japan
J. Org. Chem., Article ASAP
DOI: 10.1021/acs.joc.5b02911
Publication Date (Web): March 07, 2016
Copyright © 2016 American Chemical Society
*Tel: +81-3-5228-8715. E-mail: ssaito@rs.kagu.tus.ac.jp.
ACS Editors' Choice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

Abstract

Abstract Image
We synthesized [2]rotaxanes with a pyrrole moiety from a [2]rotaxane with a 1,3-diynyl moiety. The conversion of the 1,3-diynyl moiety of the axle component to the pyrrole moiety was accomplished by a Cu-mediated cycloaddition of anilines. The cycloaddition reaction was accelerated when the [2]rotaxane was used as the substrate. The effect of the structure of the pyrrole moiety on the rate of the shuttling was studied.
http://pubs.acs.org/doi/full/10.1021/acs.joc.5b02911
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