p-(4-Cyclohexylphenyl)aniline

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, 1440– 1443, DOI: 10.1039/jr9370001440

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

  13C NMR

 1H NMR PREDICT

 13C NMR PREDICT

 

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

Yusuke Matsuoka^†, Yuichiro Mutoh^†, Isao Azumaya^‡, Shoko Kikkawa^‡, Takeshi Kasama^§, and Shinichi Saito^*†

^† 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

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
///////

TAKE A TOUR

Nagaon, alibaug, chaul,  alibaug,  MAHARASHTRA , INDIA

Bhimeshwar temple in Nagaon

 

Bhimeshwar Temple  

Place of Worship

Address: Alibag-Revadanda Rd, Alibag, Maharashtra 402209

 

 

 

 

 

 

 

 @ Chaul Rameshwar Temple

 

 

 

 

 

 

////////