Straightforward Synthesis of Novel Biphenyl-Based Macrobicyclic Azathioethers

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.

macrocycles - sulfur - nitrogen - biphenyl

References

<A NAME="RZ14307SS-1A">1a</A> Canary JW. Gibb BC. Prog. Inorg. Chem.  1997,  45:  1 

<A NAME="RZ14307SS-1B">1b</A> Wieser C. Dieleman CB. Matt D. Coord. Chem. Rev.  1997,  165:  93 

<A NAME="RZ14307SS-1C">1c</A> Hecht S. Fréchet JMJ. Angew. Chem. Int. Ed.  2001,  40:  74 ; Angew. Chem. 2001, 113, 76

<A NAME="RZ14307SS-2A">2a</A> Reetz MT. Waldvogel SR. Angew. Chem. Int. Ed. Engl.  1997,  36:  865 ; Angew. Chem. 1997, 109, 870

<A NAME="RZ14307SS-2B">2b</A> Reetz MT. Catal. Today  1998,  42:  399 

<A NAME="RZ14307SS-2C">2c</A> Engeldinger E. Armspach D. Matt D. Angew. Chem. Int Ed.  2001,  40:  2526 ; Angew. Chem. 2001, 113, 2594

<A NAME="RZ14307SS-2D">2d</A> Slagt VF. Reek JNH. Kramer PCJ. van Leeuwen PWNM. Angew. Chem. Int. Ed.  2001,  40:  4271 ; Angew. Chem. 2001, 113, 4401

<A NAME="RZ14307SS-2E">2e</A> Yoshizawa M. Takeyama Y. Kusukawa T. Fujita M. Angew. Chem. Int. Ed.  2002,  41:  1347 ; Angew. Chem. 2002, 114, 1403

<A NAME="RZ14307SS-2F">2f</A> Ooi T. Kondo Y. Maruoka K. Angew. Chem. Int. Ed.  1998,  37:  3039 ; Angew. Chem. 1998, 110, 3213

<A NAME="RZ14307SS-3A">3a</A> 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

<A NAME="RZ14307SS-3B">3b</A> Rondelez Y. Bertho G. Reinaud O. Angew. Chem. Int. Ed.  2002,  41:  1044 ; Angew. Chem. 2002, 114, 1086

<A NAME="RZ14307SS-3C">3c</A> Rondelez Y. Rager M.-N. Duprat A. Reinaud O. J. Am. Chem. Soc.  2002,  124:  1334 

<A NAME="RZ14307SS-4A">4a</A> Kersting B. Steinfeld G. Chem. Commun.  2001,  1376 

<A NAME="RZ14307SS-4B">4b</A> Kersting B. Steinfeld G. Inorg. Chem.  2002,  41:  1140 

<A NAME="RZ14307SS-5">5</A> Klingele MH. Steinfeld G. Kersting B. Z. Naturforsch.  2001,  56b:  901 

<A NAME="RZ14307SS-6A">6a</A> Kersting B. Angew. Chem. Int. Ed.  2001,  40:  3987 ; Angew. Chem. 2001, 113, 4109

<A NAME="RZ14307SS-6B">6b</A> Steinfeld G. Lozan V. Kersting B. Angew. Chem. Int. Ed.  2003,  42:  2261 ; Angew. Chem. 2003, 115, 2363

<A NAME="RZ14307SS-6C">6c</A> Käss S. Gregor T. Kersting B. Angew. Chem. Int. Ed.  2006,  45:  101 ; Angew. Chem. 2006, 118, 107

<A NAME="RZ14307SS-7">7</A> Akiyama R. Kobayashi S. Angew. Chem. Int. Ed.  2001,  40:  3469 ; Angew. Chem. 2001, 113, 3577

<A NAME="RZ14307SS-8">8</A> Schmid M. Eberhardt R. Kukral J. Rieger B. Z. Naturforsch.  2002,  57b:  1141 

<A NAME="RZ14307SS-9A">9a</A> Miyaura N. Yanagi T. Suzuki A. Synth. Commun.  1981,  11:  513 

<A NAME="RZ14307SS-9B">9b</A> Old DW. Wolfe JP. Buchwald SL. J. Am. Chem. Soc.  1998,  120:  9722 

<A NAME="RZ14307SS-10">10</A> Bei X. Turner HW. Weinberg WH. Guram AS. Petersen JL. J. Org. Chem.  1999,  64:  6797 

<A NAME="RZ14307SS-11">11</A> Liang L.-C. Chien P.-S. Huang M.-H. Organometallics  2005,  24:  353 

<A NAME="RZ14307SS-12">12</A> Cho C.-H. Park H. Park M.-A. Ryoo T.-Y. Lee Y.-S. Park K. Eur. J. Org. Chem.  2005,  3177 

<A NAME="RZ14307SS-13">13</A> Sykes P. Reaktionsmechanismen der Organischen Chemie   VCH; Weinheim: 1988.  p.159-160  

<A NAME="RZ14307SS-14">14</A> Monguchi K. Itoh T. Hirai K. Tomioka H. J. Am. Chem. Soc.  2004,  126:  11900 

<A NAME="RZ14307SS-15">15</A>

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).

<A NAME="RZ14307SS-16">16</A> Klingele MH. Kersting B. Z. Naturforsch.  2001,  56b:  437 

<A NAME="RZ14307SS-17">17</A> Bankston D. Synthesis  2004,  283 

<A NAME="RZ14307SS-18">18</A> Harvey RG. Dai Q. Ran C. Penning TM. J. Org. Chem.  2004,  69:  2024 

<A NAME="RZ14307SS-19">19</A> Sander W. Exner M. Winkler M. Balster A. Hjerpe A. Kraka E. Cremer D. J. Am. Chem. Soc.  2002,  124:  13072 

<A NAME="RZ14307SS-20">20</A> Josel HP. Puff H. Franken S. Weber E. J. Org. Chem.  1985,  50:  3125 

<A NAME="RZ14307SS-21">21</A> Illuminati G. Mandolini L. Acc. Chem. Res.  1981,  14:  95 

<A NAME="RZ14307SS-22">22</A> Templated Organic Synthesis   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 2000. 

<A NAME="RZ14307SS-23">23</A> Busch DH. Stephenson NA. Coord. Chem. Rev.  1990,  100:  119 

<A NAME="RZ14307SS-24">24</A> Bonstra EG. Acta. Crystallogr.  1963,  16:  816 

<A NAME="RZ14307SS-25">25</A> Siedle G. Kersting B. Z. Anorg. Allg. Chem.  2003,  629:  2083 

<A NAME="RZ14307SS-26A">26a</A> Tellier F. Sauvetre R. Normant J.-F. J. Organomet. Chem.  1985,  292:  19 

<A NAME="RZ14307SS-26B">26b</A> Trost B. Mignami K. J. Org. Chem.  1986,  51:  3435 

<A NAME="RZ14307SS-27">27</A> Sheldrick GM. Acta Crystallogr.  1990,  A46:  467 

<A NAME="RZ14307SS-28">28</A> Sheldrick GM. SHELXL-97, Computer Program for Crystal Structure Refinement   University of Göttingen; Göttingen: 1997. 

<A NAME="RZ14307SS-29">29</A> Spek AL. PLATON - A Multipurpose Crystallographic Tool   Utrecht University; Utrecht: 2000. 

<A NAME="RZ14307SS-30">30</A> Farrugia LJ. J. Appl. Crystallogr.  1997,  30:  565 

<A NAME="RZ14307SS-31">31</A>

CCDC 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: [phone];
E-mail: [e-mail].