Subscribe to RSS
DOI: 10.1055/s-2007-990867
Straightforward Synthesis of Novel Biphenyl-Based Macrobicyclic Azathioethers
Publication History
Publication Date:
31 October 2007 (online)
Abstract
The synthesis and characterization of two new macrobicyclic azathioether ligands are reported. The biphenyl-based compounds were prepared by traditional organic reactions and cyclization methods. The identity of one compound was confirmed by X-ray crystallography.
Key words
macrocycles - sulfur - nitrogen - biphenyl
-
1a
Canary JW.Gibb BC. Prog. Inorg. Chem. 1997, 45: 1 -
1b
Wieser C.Dieleman CB.Matt D. Coord. Chem. Rev. 1997, 165: 93 -
1c
Hecht S.Fréchet JMJ. Angew. Chem. Int. Ed. 2001, 40: 74 ; Angew. Chem. 2001, 113, 76 -
2a
Reetz MT.Waldvogel SR. Angew. Chem. Int. Ed. Engl. 1997, 36: 865 ; Angew. Chem. 1997, 109, 870 -
2b
Reetz MT. Catal. Today 1998, 42: 399 -
2c
Engeldinger E.Armspach D.Matt D. Angew. Chem. Int Ed. 2001, 40: 2526 ; Angew. Chem. 2001, 113, 2594 -
2d
Slagt VF.Reek JNH.Kramer PCJ.van Leeuwen PWNM. Angew. Chem. Int. Ed. 2001, 40: 4271 ; Angew. Chem. 2001, 113, 4401 -
2e
Yoshizawa M.Takeyama Y.Kusukawa T.Fujita M. Angew. Chem. Int. Ed. 2002, 41: 1347 ; Angew. Chem. 2002, 114, 1403 -
2f
Ooi T.Kondo Y.Maruoka K. Angew. Chem. Int. Ed. 1998, 37: 3039 ; Angew. Chem. 1998, 110, 3213 -
3a
Blanchard S.Le Clainche L.Rager M.-N.Chansou B.Tuchagues J.-P.Duprat AF.Le Mest Y.Reinaud O. Angew. Chem., Int. Ed. Engl. 1998, 37: 2732 ; Angew. Chem. 1998, 110, 2861 -
3b
Rondelez Y.Bertho G.Reinaud O. Angew. Chem. Int. Ed. 2002, 41: 1044 ; Angew. Chem. 2002, 114, 1086 -
3c
Rondelez Y.Rager M.-N.Duprat A.Reinaud O. J. Am. Chem. Soc. 2002, 124: 1334 -
4a
Kersting B.Steinfeld G. Chem. Commun. 2001, 1376 -
4b
Kersting B.Steinfeld G. Inorg. Chem. 2002, 41: 1140 - 5
Klingele MH.Steinfeld G.Kersting B. Z. Naturforsch. 2001, 56b: 901 -
6a
Kersting B. Angew. Chem. Int. Ed. 2001, 40: 3987 ; Angew. Chem. 2001, 113, 4109 -
6b
Steinfeld G.Lozan V.Kersting B. Angew. Chem. Int. Ed. 2003, 42: 2261 ; Angew. Chem. 2003, 115, 2363 -
6c
Käss S.Gregor T.Kersting B. Angew. Chem. Int. Ed. 2006, 45: 101 ; Angew. Chem. 2006, 118, 107 - 7
Akiyama R.Kobayashi S. Angew. Chem. Int. Ed. 2001, 40: 3469 ; Angew. Chem. 2001, 113, 3577 - 8
Schmid M.Eberhardt R.Kukral J.Rieger B. Z. Naturforsch. 2002, 57b: 1141 -
9a
Miyaura N.Yanagi T.Suzuki A. Synth. Commun. 1981, 11: 513 -
9b
Old DW.Wolfe JP.Buchwald SL. J. Am. Chem. Soc. 1998, 120: 9722 - 10
Bei X.Turner HW.Weinberg WH.Guram AS.Petersen JL. J. Org. Chem. 1999, 64: 6797 - 11
Liang L.-C.Chien P.-S.Huang M.-H. Organometallics 2005, 24: 353 - 12
Cho C.-H.Park H.Park M.-A.Ryoo T.-Y.Lee Y.-S.Park K. Eur. J. Org. Chem. 2005, 3177 - 13
Sykes P. Reaktionsmechanismen der Organischen Chemie VCH; Weinheim: 1988. p.159-160 - 14
Monguchi K.Itoh T.Hirai K.Tomioka H. J. Am. Chem. Soc. 2004, 126: 11900 - 16
Klingele MH.Kersting B. Z. Naturforsch. 2001, 56b: 437 - 17
Bankston D. Synthesis 2004, 283 - 18
Harvey RG.Dai Q.Ran C.Penning TM. J. Org. Chem. 2004, 69: 2024 - 19
Sander W.Exner M.Winkler M.Balster A.Hjerpe A.Kraka E.Cremer D. J. Am. Chem. Soc. 2002, 124: 13072 - 20
Josel HP.Puff H.Franken S.Weber E. J. Org. Chem. 1985, 50: 3125 - 21
Illuminati G.Mandolini L. Acc. Chem. Res. 1981, 14: 95 - 22
Templated Organic Synthesis
Diederich F.Stang PJ. Wiley-VCH; Weinheim: 2000. - 23
Busch DH.Stephenson NA. Coord. Chem. Rev. 1990, 100: 119 - 24
Bonstra EG. Acta. Crystallogr. 1963, 16: 816 - 25
Siedle G.Kersting B. Z. Anorg. Allg. Chem. 2003, 629: 2083 -
26a
Tellier F.Sauvetre R.Normant J.-F. J. Organomet. Chem. 1985, 292: 19 -
26b
Trost B.Mignami K. J. Org. Chem. 1986, 51: 3435 - 27
Sheldrick GM. Acta Crystallogr. 1990, A46: 467 - 28
Sheldrick GM. SHELXL-97, Computer Program for Crystal Structure Refinement University of Göttingen; Göttingen: 1997. - 29
Spek AL. PLATON - A Multipurpose Crystallographic Tool Utrecht University; Utrecht: 2000. - 30
Farrugia LJ. J. Appl. Crystallogr. 1997, 30: 565
References
Preliminary analytical data for 5: Mp 76 °C. 1H NMR (400 MHz, CDCl3): δ = 1.36 (s, 9 H, CH3), 2.39 (s, 3 H, CH3), 2.72 (s, 3 H, CH3), 7.07 (s, 1 H, ArH), 7.27 (d, J = 8.0 Hz, 2 H, ArH), 7.42 (d, J = 8.0 Hz, 2 H, ArH).
31CCDC 648984 contains the supplementary crystallographic data for compound L
³
. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallgraphic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033;
E-mail: deposit@ccdc.cam.ac.uk.