Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2013; 24(18): 2365-2369
DOI: 10.1055/s-0033-1339695
DOI: 10.1055/s-0033-1339695
letter
ortho-Substituted 1,8-Diarylnaphthalenes: Conformational Thermodynamics and Kinetics
Further Information
Publication History
Received: 17 July 2013
Accepted after revision: 13 August 2013
Publication Date:
03 September 2013 (online)
![](https://www.thieme-connect.de/media/synlett/201318/lookinside/thumbnails/10.1055-s-0033-1339695-1.jpg)
Abstract
1,8-Diarylnaphthalenes show interesting potential as chiral sensors, environment sensors and stereodynamic switches. The kinetics and thermodynamics of the conformational equilibria of two such compounds are described. These compounds, along with others reported previously, show that several features can be used to tune the conformational behaviour of these compounds, giving the possibility to design molecules for specific applications in the future.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1a Cozzi F, Ponzini F, Annunziata R, Cinquini M, Siegel JS. Angew. Chem., Int. Ed. Engl. 1995; 34: 1019
- 1b Cozzi F, Siegel JS. Pure Appl. Chem. 1995; 67: 683
- 1c Annunziata R, Ponzini F, Raimondi L. Magn. Reson. Chem. 1995; 33: 297
- 1d Cozzi F, Cinquini M, Annuziata R, Siegal JS. J. Am. Chem. Soc. 1993; 115: 5330
- 1e Cozzi F, Cinquini M, Annunziata R, Dywer T, Siegel JS. J. Am. Chem. Soc. 1992; 114: 5729
- 1f Lima CF. R. A. C, Gomes LR, Low JN, Silva AM. S, Santos LM. N. B. F. J. Org. Chem. 2012; 77: 10422
- 1g Lima CF. R. A. C, Rocha MA. A, Gomes LR, Low JN, Silva AM. S, Santos LM. N. B. F. Chem. Eur. J. 2012; 18: 8934
- 2 Wolf C, Mei X. J. Am. Chem. Soc. 2003; 125: 10651
- 3a House HO, Koepsell DG, Campbell WJ. J. Org. Chem. 1972; 37: 1003
- 3b House HO, Campbell WJ, Gall M. J. Org. Chem. 1970; 35: 1815
- 4 Clough RL, Roberts JD. J. Am. Chem. Soc. 1976; 98: 1018
- 5a Thirsk C, Hawkes GE, Kroemer RT, Liedl KR, Loerting T, Nasser R, Pritchard RG, Steele M, Warren JE, Whiting A. J. Chem. Soc., Perkin Trans. 2 2002; 1510
- 5b Steele M, Watkinson M, Whiting A. J. Chem. Soc., Perkin Trans. 1 2001; 6: 588
- 6a Mei X, Martin RM, Wolf C. J. Org. Chem. 2006; 71: 2854
- 6b Tumambac GE, Wolf C. J. Org Chem. 2005; 70: 2930
- 6c Mei X, Wolf C. J. Org. Chem. 2005; 70: 2299
- 6d Tumambac GE, Wolf C. J. Org. Chem. 2004; 69: 2048
- 7a Zoltewicz JA, Maier NM, Lavieri S, Ghivirigia I, Abboud KA, Fabian WM. F. Tetrahedron 1997; 53: 5379
- 7b Katoh T, Ogawa K, Inagaki Y, Okazaki R. Tetrahedron 1997; 53: 3557
- 7c Zoltewicz JA, Maier NM, Fabian WM. F. J. Org. Chem. 1997; 62: 3215
- 7d Zoltewicz JA, Maier NM, Fabian WM. F. Tetrahedron 1996; 52: 8703
- 7e Zoltewicz JA, Maier NM, Fabian WM. F. J. Org. Chem. 1996; 61: 7018
- 7f Wahl P, Krieger C, Schweitzer D, Staab HA. Chem. Ber. 1984; 117: 260
- 8 Zoltewicz JA, Maier NM, Fabien WM. F. J. Org. Chem. 1998; 63: 4985
- 9 Terrasson V, Prim D, Marrot J. Eur. J. Inorg. Chem. 2008; 2739
- 10 Pieters G, Terrasson V, Gaucher A, Prim D, Marrot J. Eur. J. Org. Chem. 2010; 5800
- 11 Anslyn EV, Dougherty DA. Modern Physical Organic Chemistry . University Science Books; Sausalito, CA: 2006: 104
- 12 Cook JL, Hunter CA, Low CM. R, Perez-Velasco A, Vinter JG. Angew. Chem. Int. Ed. 2007; 46: 3705