Synthesis of Crown-Ester-Bipyridines and Crown-Ester-Viologens

Stefan H. Bossmann; Heinz Dürr; Megh Raj Pokhrel

doi:10.1055/s-2005-861829

PAPER

Synthesis of Crown-Ester-Bipyridines and Crown-Ester-Viologens

Stefan H. Bossmann*^a, Heinz Dürr^b, Megh Raj Pokhrel^c
^a Kansas State University, Department of Chemistry, 111 Willard Hall, Manhattan, Kansas 66506-3701, USA
Fax: +1(785)5326666; e-Mail: sbossman@ksu.edu;
^b University of Saarland, Department of Chemistry, Section of Organic Chemistry, 66041 Saarbrücken, Germany
e-Mail: h.duerr@rz.uni-sb.de;
^c Central Department of Chemistry, Tribhuvan University, Kirtipur, Kathmandu, Nepal
e-Mail: meghraj11@hotmail.com;

Abstract

All articles of this category

Abstract

Six novel 4,4′-bipyridine-crown-esters, derived from [4,4′]bipyridinyl-3,3′-dicarboxylic acid, [4,4′]bipyridinyl-2,2′-dicarboxylic acid and [4,4′]bipyridinyl-2,2′,6,6′-tetra-carboxylic acid were synthesized employing a procedure closely related to the ‘cesium carbonate method’. The 4,4′-bipyridine-crown-esters differ in their substitution positions of the aromatic bipyridine-units, as well as in the geometric extensions of their crown-ester moieties. Addition of 1,3-propane sultone to the 4,4′-bipyridine-crown-esters resulted in five novel propanesultonated 4,4′-bipyridine-crown-ester viologens.

Key words

alkylations - bipyridines - esters - nickel(0) - viologens

Full Text

References

Former address: University of Karlsruhe, Department of Chemical & Process Engineering, 76128 Karlsruhe, Germany.

<A NAME="RM08904SS-2">2</A> Rebek JJ. Wattley RV. Heterocycl. Chem. 1980, 17: 749

<A NAME="RM08904SS-3">3</A> Newkome GR. Kohli DK. Fronczek FR. Hales BJ. Case EE. Chiari G. J. Am. Chem. Soc. 1980, 102: 7608

<A NAME="RM08904SS-4A">4a</A> Rebek JJ. Marshall L. J. Am. Chem. Soc. 1983, 105: 6668

<A NAME="RM08904SS-4B">4b</A> Rebek JJ. Costello T. Wattley RV. J. Am. Chem. Soc. 1985, 107: 7487

<A NAME="RM08904SS-4C">4c</A> Newkome GR. Keifer GE. Kohli DK. Xia YJ. Fronczek FR. Baker GR. J. Org. Chem. 1989, 54: 5105

<A NAME="RM08904SS-5A">5a</A> Frontiers in Supramolecular Chemistry and Photochemistry Dürr H. Schneider H.-J. VCH; Weinheim, New York: 1991.

<A NAME="RM08904SS-5B">5b</A> Willner I. Kaganer E. Joselevich E. Dürr H. David E. Gunter MJ. Johnston MR. Coord. Chem. Rev. 1998, 171: 261

<A NAME="RM08904SS-5C">5c</A> Dürr H. Bossmann SH. Acc. Chem. Res. 2001, 34: 905

<A NAME="RM08904SS-6A">6a</A> Chelucci G. Thummel RP. Chem. Rev. 2002, 102: 3129

<A NAME="RM08904SS-6B">6b</A> Juris A. Balzani V. Barigelletti F. Campagna S. Belser P. von Zelewsky A. Coord. Chem. Rev. 1988, 84: 85

<A NAME="RM08904SS-6C">6c</A> Schubert US. Eschbaumer C. Angew. Chem. Int. Ed. 2002, 41: 2892

<A NAME="RM08904SS-7A">7a</A> Simpson NRM. Ward MD. Morales AF. Ventura B. Barigelletti F. J. Chem. Soc., Dalton Trans. 2002, 2455

<A NAME="RM08904SS-7B">7b</A> Berg-Brennan CA. Yoon DI. Slone RV. Kazala AP. Hupp JT. Inorg. Chem. 1996, 35: 2032

<A NAME="RM08904SS-7C">7c</A> Bossmann SH. Seiler M. Dürr H. J. Phys. Org. Chem. 1992, 5: 63

<A NAME="RM08904SS-8">8</A> Newkome GR. Keifer GE. Kohli DK. Xia YJ. Fronczek FR. Baker GR. J. Org. Chem. 1989, 54: 5105

<A NAME="RM08904SS-9">9</A> Hu Y.-Z. Bossmann SH. von Loyen D. Schwarz O. Dürr H. Eur. J. Chem. 1999, 5: 1137

<A NAME="RM08904SS-10">10</A> Chiba M. Ogawa K. Tsuge K. Abe M. Kim H.-B. Sasaki Y. Kitamura N. Chem. Lett. 2001, 692

<A NAME="RM08904SS-11">11</A> Chiba M. Kim H.-B. Kitamura N. Anal. Sci. 2002, 18: 461

<A NAME="RM08904SS-12">12</A> Fischer C. Sarti G. Casnati A. Carrettoni B. Manet I. Schuurman R. Guardigli M. Sabbatini N. Ungaro R. Chem.-Eur. J. 2000, 6: 1026

<A NAME="RM08904SS-13A">13a</A> McAskill NA. Aust. J. Chem. 1984, 37: 1579

<A NAME="RM08904SS-13B">13b</A> Willner I. Maidan R. Mandler D. Dürr H. Dorr G. Zengerle K. J. Am. Chem. Soc. 1987, 109: 6080

<A NAME="RM08904SS-13C">13c</A> Felderhoff M. Heinen S. Molisho N. Webersinn S. Walder L. Helv. Chim. Acta 2000, 83: 181

<A NAME="RM08904SS-14">14</A> Willner I. Ford J. J. Heterocycl. Chem. 1983, 20: 1113

<A NAME="RM08904SS-15A">15a</A> Dürr H. Kilburg H. Bossmann SH. Synthesis 1990, 773

<A NAME="RM08904SS-15B">15b</A> Dürr H. Thome A. Kranz C. Bossmann SH. Kilburg H. Braun B. Janzen K.-P. Blasius E. J. Phys. Org. Chem. 1992, 5: 689

<A NAME="RM08904SS-15C">15c</A> Bossmann SH. Seiler M. Dürr H. J. Phys. Org. Chem. 1992, 5: 63

<A NAME="RM08904SS-16">16</A> Kruizinga WH. Kellogg RM. J. Am. Chem. Soc. 1981, 103: 5183

<A NAME="RM08904SS-17">17</A> Willner I. Ayalon A. Rabinovitz M. New J. Chem. 1990, 14: 685

<A NAME="RM08904SS-18A">18a</A> Kende AS. Liebeskind LS. Braitsch DM. Tetrahedron Lett. 1975, 39: 3375

<A NAME="RM08904SS-18B">18b</A> Tiecco M. Testaferri L. Tingoli M. Chianelli D. Montanucci M. Synthesis 1984, 736

<A NAME="RM08904SS-19">19</A> Hünig S. Wehner I. Synthesis 1989, 552

<A NAME="RM08904SS-20">20</A> Singh N. Lee DG. Org. Process Res. Dev. 2001, 5: 599

<A NAME="RM08904SS-21A">21a</A> Bradshaw JS. Krakowiak KE. Izatt RM. Bruening RL. Tarbet BJ. J. Heterocycl. Chem. 1990, 27: 347

<A NAME="RM08904SS-21B">21b</A> Mills OS. Mooney NJ. Robinson PM. Watt CIF. Box BG. J. Chem. Soc., Perkin. Trans. 2 1995, 697

<A NAME="RM08904SS-22">22</A> Leighton P. Sanders JKM. J. Chem. Soc., Perkin. Trans. 1 1987, 2385