Synthesis of a biphenyl-based cyclophane via benzidine rearrangement of a constrained m-nitrophenol derivative

Tetrahedron Letters

Volumn 44, Issue 13, 2003, Pages 2665-2667

  Benniston, Andrew C ^a   Clegg, William ^a   Harriman, Anthony ^a   Harrington, Ross W ^a   Li, Peiyi ^a   Sams, Craig ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Benzidine rearrangement; Cyclophane; Supramolecular chemistry

Indexed keywords

BENZIDINE; BIPHENYL; CYCLOPHANE; NITROPHENOL; POLYETHER;

ARTICLE; CHEMICAL MODIFICATION; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0037463747     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00343-5     Document Type: Article

References (17)

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6. A detailed search using SciFinder and Beilstein identified several 4,4′-biphenol-based cyclophanes, but none with only a polyether or alkyl strap. For other examples see: Neumann, B.; Hegmann, T.; Wolf, R.; Tschierske, C. Chem. Commun. 1998, 105-106; Abd-El-Aziz, A. S.; de Denus, C. R.; Zaworotko, M. J.; Sharma, C. V. K. Chem. Commun. 1998, 265-266; Nishikido, J.; Inazu, T.; Yoshino, T. Bull. Chim. Soc. Jpn. 1973, 46, 263-265; Siepen, A.; Zett, A.; Vögtle, F. Leibigs Ann. Chem. 1996, 757-760; Ashton, P. R.; Joachimi, D.; Spencer, N.; Stoddart, J. F.; Tscierske, C.; White, A. J. P.; Williams, D. J.; Zab, K. Angew. Chem., Int. Ed. 1994, 106, 1503-1506.
7. A detailed search using SciFinder and Beilstein identified several 4,4′-biphenol-based cyclophanes, but none with only a polyether or alkyl strap. For other examples see: Neumann, B.; Hegmann, T.; Wolf, R.; Tschierske, C. Chem. Commun. 1998, 105-106; Abd-El-Aziz, A. S.; de Denus, C. R.; Zaworotko, M. J.; Sharma, C. V. K. Chem. Commun. 1998, 265-266; Nishikido, J.; Inazu, T.; Yoshino, T. Bull. Chim. Soc. Jpn. 1973, 46, 263-265; Siepen, A.; Zett, A.; Vögtle, F. Leibigs Ann. Chem. 1996, 757-760; Ashton, P. R.; Joachimi, D.; Spencer, N.; Stoddart, J. F.; Tscierske, C.; White, A. J. P.; Williams, D. J.; Zab, K. Angew. Chem., Int. Ed. 1994, 106, 1503-1506.
8. A detailed search using SciFinder and Beilstein identified several 4,4′-biphenol-based cyclophanes, but none with only a polyether or alkyl strap. For other examples see: Neumann, B.; Hegmann, T.; Wolf, R.; Tschierske, C. Chem. Commun. 1998, 105-106; Abd-El-Aziz, A. S.; de Denus, C. R.; Zaworotko, M. J.; Sharma, C. V. K. Chem. Commun. 1998, 265-266; Nishikido, J.; Inazu, T.; Yoshino, T. Bull. Chim. Soc. Jpn. 1973, 46, 263-265; Siepen, A.; Zett, A.; Vögtle, F. Leibigs Ann. Chem. 1996, 757-760; Ashton, P. R.; Joachimi, D.; Spencer, N.; Stoddart, J. F.; Tscierske, C.; White, A. J. P.; Williams, D. J.; Zab, K. Angew. Chem., Int. Ed. 1994, 106, 1503-1506.
9. A detailed search using SciFinder and Beilstein identified several 4,4′-biphenol-based cyclophanes, but none with only a polyether or alkyl strap. For other examples see: Neumann, B.; Hegmann, T.; Wolf, R.; Tschierske, C. Chem. Commun. 1998, 105-106; Abd-El-Aziz, A. S.; de Denus, C. R.; Zaworotko, M. J.; Sharma, C. V. K. Chem. Commun. 1998, 265-266; Nishikido, J.; Inazu, T.; Yoshino, T. Bull. Chim. Soc. Jpn. 1973, 46, 263-265; Siepen, A.; Zett, A.; Vögtle, F. Leibigs Ann. Chem. 1996, 757-760; Ashton, P. R.; Joachimi, D.; Spencer, N.; Stoddart, J. F.; Tscierske, C.; White, A. J. P.; Williams, D. J.; Zab, K. Angew. Chem., Int. Ed. 1994, 106, 1503-1506.
10. A detailed search using SciFinder and Beilstein identified several 4,4′-biphenol-based cyclophanes, but none with only a polyether or alkyl strap. For other examples see: Neumann, B.; Hegmann, T.; Wolf, R.; Tschierske, C. Chem. Commun. 1998, 105-106; Abd-El-Aziz, A. S.; de Denus, C. R.; Zaworotko, M. J.; Sharma, C. V. K. Chem. Commun. 1998, 265-266; Nishikido, J.; Inazu, T.; Yoshino, T. Bull. Chim. Soc. Jpn. 1973, 46, 263-265; Siepen, A.; Zett, A.; Vögtle, F. Leibigs Ann. Chem. 1996, 757-760; Ashton, P. R.; Joachimi, D.; Spencer, N.; Stoddart, J. F.; Tscierske, C.; White, A. J. P.; Williams, D. J.; Zab, K. Angew. Chem., Int. Ed. 1994, 106, 1503-1506.
11. +).
12. Computational studies on products and intermediates were carried out using the commercial package Titan at the semi-empirical AM1 level. Typically, a structure was allowed to energy-minimise and converge, and a single-point calculation carried out to determine the enthalpy of formation.
13. Preliminary HPLC separations carried out on the mixtures suggest that products could be isolated on a preparative scale and fully identified.
14. +).
15. The product from the Sandmeyer reaction using 5A was identified as the iodonium salt 5AII (yield=31%). The overall molecular structure however was similar in appearance to that of the diiodide 2AI.
16. -3.
17. Cotton F.A., Wilkinson G. Advanced Inorganic Chemistry - A Comprehensive Edition. 4th ed. 1980;14 John Wiley & Sons.