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
References 1 Former address: University of Karlsruhe, Department of Chemical & Process Engineering, 76128 Karlsruhe, Germany.
2 Rebek JJ.
Wattley RV.
Heterocycl. Chem.
1980,
17:
749
3 Newkome GR.
Kohli DK.
Fronczek FR.
Hales BJ.
Case EE.
Chiari G.
J. Am. Chem. Soc.
1980,
102:
7608
4a Rebek JJ.
Marshall L.
J. Am. Chem. Soc.
1983,
105:
6668
4b Rebek JJ.
Costello T.
Wattley RV.
J. Am. Chem. Soc.
1985,
107:
7487
4c Newkome GR.
Keifer GE.
Kohli DK.
Xia YJ.
Fronczek FR.
Baker GR.
J. Org. Chem.
1989,
54:
5105
5a Frontiers in Supramolecular Chemistry and Photochemistry
Dürr H.
Schneider H.-J.
VCH;
Weinheim, New York:
1991.
5b Willner I.
Kaganer E.
Joselevich E.
Dürr H.
David E.
Gunter MJ.
Johnston MR.
Coord. Chem. Rev.
1998,
171:
261
5c Dürr H.
Bossmann SH.
Acc. Chem. Res.
2001,
34:
905
6a Chelucci G.
Thummel RP.
Chem. Rev.
2002,
102:
3129
6b Juris A.
Balzani V.
Barigelletti F.
Campagna S.
Belser P.
von Zelewsky A.
Coord. Chem. Rev.
1988,
84:
85
6c Schubert US.
Eschbaumer C.
Angew. Chem. Int. Ed.
2002,
41:
2892
7a Simpson NRM.
Ward MD.
Morales AF.
Ventura B.
Barigelletti F.
J. Chem. Soc., Dalton Trans.
2002,
2455
7b Berg-Brennan CA.
Yoon DI.
Slone RV.
Kazala AP.
Hupp JT.
Inorg. Chem.
1996,
35:
2032
7c Bossmann SH.
Seiler M.
Dürr H.
J. Phys. Org. Chem.
1992,
5:
63
8 Newkome GR.
Keifer GE.
Kohli DK.
Xia YJ.
Fronczek FR.
Baker GR.
J. Org. Chem.
1989,
54:
5105
9 Hu Y.-Z.
Bossmann SH.
von Loyen D.
Schwarz O.
Dürr H.
Eur. J. Chem.
1999,
5:
1137
10 Chiba M.
Ogawa K.
Tsuge K.
Abe M.
Kim H.-B.
Sasaki Y.
Kitamura N.
Chem. Lett.
2001,
692
11 Chiba M.
Kim H.-B.
Kitamura N.
Anal. Sci.
2002,
18:
461
12 Fischer C.
Sarti G.
Casnati A.
Carrettoni B.
Manet I.
Schuurman R.
Guardigli M.
Sabbatini N.
Ungaro R.
Chem.-Eur. J.
2000,
6:
1026
13a McAskill NA.
Aust. J. Chem.
1984,
37:
1579
13b Willner I.
Maidan R.
Mandler D.
Dürr H.
Dorr G.
Zengerle K.
J. Am. Chem. Soc.
1987,
109:
6080
13c Felderhoff M.
Heinen S.
Molisho N.
Webersinn S.
Walder L.
Helv. Chim. Acta
2000,
83:
181
14 Willner I.
Ford J.
J. Heterocycl. Chem.
1983,
20:
1113
15a Dürr H.
Kilburg H.
Bossmann SH.
Synthesis
1990,
773
15b Dürr H.
Thome A.
Kranz C.
Bossmann SH.
Kilburg H.
Braun B.
Janzen K.-P.
Blasius E.
J. Phys. Org. Chem.
1992,
5:
689
15c Bossmann SH.
Seiler M.
Dürr H.
J. Phys. Org. Chem.
1992,
5:
63
16 Kruizinga WH.
Kellogg RM.
J. Am. Chem. Soc.
1981,
103:
5183
17 Willner I.
Ayalon A.
Rabinovitz M.
New J. Chem.
1990,
14:
685
18a Kende AS.
Liebeskind LS.
Braitsch DM.
Tetrahedron Lett.
1975,
39:
3375
18b Tiecco M.
Testaferri L.
Tingoli M.
Chianelli D.
Montanucci M.
Synthesis
1984,
736
19 Hünig S.
Wehner I.
Synthesis
1989,
552
20 Singh N.
Lee DG.
Org. Process Res. Dev.
2001,
5:
599
21a Bradshaw JS.
Krakowiak KE.
Izatt RM.
Bruening RL.
Tarbet BJ.
J. Heterocycl. Chem.
1990,
27:
347
21b Mills OS.
Mooney NJ.
Robinson PM.
Watt CIF.
Box BG.
J. Chem. Soc., Perkin. Trans. 2
1995,
697
22 Leighton P.
Sanders JKM.
J. Chem. Soc., Perkin. Trans. 1
1987,
2385
