Monatshefte für Chemie - Chemical Monthly

, Volume 143, Issue 6, pp 901–908 | Cite as

On the isomerization of a trans-dichloro to a cis-dichloro amide-chelated ruthenium benzylidene complex and the catalytic scope of these species in olefin metathesis

Original Paper

Abstract

Upon comparative NMR spectroscopy studies, the isomerization of newly disclosed dichloro [κ2(C,O)-2-(N-propylaminocarbonyl)benzylidene][1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]ruthenium from trans-dichloro configuration (SPY-5-31) to its thermodynamically more favored cis-dichloro derivative (with SPY-5-34 stereochemistry) was found to proceed via dissociation of one chloride ligand to form an intermediate cationic species. Furthermore, the performance of the trans- and the cis-dichloro derivatives as catalysts in ring-closing metathesis and as initiators in ring-opening metathesis polymerization was studied.

Graphical abstract

Keywords

Organometallic compounds Homogeneous catalysis Structure–activity relationships Polymerizations 

Notes

Acknowledgments

Financial support by the European Community (Grant no. CP-FP 211468-2 EUMET) is gratefully acknowledged.

References

  1. 1.
    Grubbs RH (2003) Handbook of metathesis, vol 1–3. Wiley, WeinheimCrossRefGoogle Scholar
  2. 2.
    Trnka TM, Grubbs RH (2001) Acc Chem Res 34:18CrossRefGoogle Scholar
  3. 3.
    Burtscher D, Grela K (2009) Angew Chem Int Ed 48:442CrossRefGoogle Scholar
  4. 4.
    Hansen SM, Rominger F, Metz M, Hofmann P (1995) Chem Eur J 5:557CrossRefGoogle Scholar
  5. 5.
    Hansen SM, Volland MAO, Rominger F, Eisenträger F, Hofmann P (1999) Angew Chem Int Ed 38:1273CrossRefGoogle Scholar
  6. 6.
    Prühs S, Lehmann CW, Fürstner A (2004) Organometallics 23:280CrossRefGoogle Scholar
  7. 7.
    Slugovc C, Perner B, Stelzer F, Mereiter K (2004) Organometallics 23:3622CrossRefGoogle Scholar
  8. 8.
    Amoroso D, Jabri A, Yap GPA, Gusev DG, dos Santos EN, Fogg DE (2004) Organometallics 23:4047CrossRefGoogle Scholar
  9. 9.
    Ung T, Hejl A, Grubbs RH, Schrodi Y (2004) Organometallics 23:5399CrossRefGoogle Scholar
  10. 10.
    Barbasiewicz M, Szadkowska A, Bujok R, Grela K (2006) Organometallics 25:3599CrossRefGoogle Scholar
  11. 11.
    Gstrein X, Burtscher D, Szadkowska A, Barbasiewicz M, Stelzer F, Grela K, Slugovc C (2007) J Polym Sci Part A Polym Chem 45:3494CrossRefGoogle Scholar
  12. 12.
    Ben-Asuly A, Tzur E, Diesendruck CE, Sigalov M, Goldberg I, Lemcoff NG (2008) Organometallics 27:811CrossRefGoogle Scholar
  13. 13.
    Diesendruck CE, Vidavsky Y, Ben-Asuly A, Lemcoff NG (2009) J Polym Sci Part A Polym Chem 47:4209CrossRefGoogle Scholar
  14. 14.
    Bantreil X, Schmid TE, Randall RAM, Slawin AMZ, Cazin CSJ (2010) Chem Commun 46:7115CrossRefGoogle Scholar
  15. 15.
    Leitgeb A, Wappel J, Slugovc C (2010) Polymer 51:2927CrossRefGoogle Scholar
  16. 16.
    Leitgeb A, Szadkowska A, Michalak M, Barbasiewicz M, Grela K, Slugovc C (2011) J Polym Sci Part A Polym Chem 49:3448CrossRefGoogle Scholar
  17. 17.
    Monsaert S, Lozano Vila A, Drozdzak R, Voort Van Der P, Verpoort F (2009) Chem Soc Rev 38:3360CrossRefGoogle Scholar
  18. 18.
    Vidavsky Y, Anaby A, Lemcoff NG (2012) Dalton Trans 41:32CrossRefGoogle Scholar
  19. 19.
    Abbas M, Slugovc C (2011) Tetrahedron Lett 52:2560CrossRefGoogle Scholar
  20. 20.
    Abbas M, Slugovc C (2012) Monatsh Chem. doi: 10.1007/s00706-011-0717-x Google Scholar
  21. 21.
    Ben-Asuly A, Aharoni A, Diesendruck CE, Vidavsky Y, Goldberg I, Straub BF, Lemcoff NG (2009) Organometallics 28:4652CrossRefGoogle Scholar
  22. 22.
    Benitez D, Tkatchouk E, Goddard WA III (2008) Chem Commun 46:6194–6196CrossRefGoogle Scholar
  23. 23.
    Poater A, Ragone F, Correa A, Szadkowska A, Barbasiewicz M, Grela K, Cavallo L (2010) Chem Eur J 16:14354CrossRefGoogle Scholar
  24. 24.
    Benitez D, Goddard WA III (2005) J Am Chem Soc 127:12218CrossRefGoogle Scholar
  25. 25.
    Zirngast M, Pump E, Leitgeb A, Albering JH, Slugovc C (2011) Chem Commun 47:2261CrossRefGoogle Scholar
  26. 26.
    Kattnig E, Albert M (2004) Org Lett 6:945CrossRefGoogle Scholar
  27. 27.
    Kerins F, O’Sheah DF (2002) J Org Chem 67:4968CrossRefGoogle Scholar
  28. 28.
    Garber SB, Kingsbury JS, Gray LB, Hoveyda AH (2000) J Am Chem Soc 122:8169CrossRefGoogle Scholar
  29. 29.
    Aharoni A, Vidavsky Y, Diesendruck CE, Ben-Asuly A, Goldberg I, Lemcoff NG (2011) Organometallics 30:1607CrossRefGoogle Scholar
  30. 30.
    Fürstner A, Thiel OR, Lehmann CW (2002) Organometallics 21:331CrossRefGoogle Scholar
  31. 31.
    Hong SH, Sanders DP, Lee CW, Grubbs RH (2005) J Am Chem Soc 127:17160CrossRefGoogle Scholar
  32. 32.
    Burtscher D, Lexer C, Mereiter K, Winde R, Karch R, Slugovc C (2008) J Polym Sci Part A Polym Chem 46:4630CrossRefGoogle Scholar
  33. 33.
    Urbina-Blanco CA, Manzini S, Pérez Gomes J, Doppiu A, Nolan SP (2011) Chem Commun 47:5022CrossRefGoogle Scholar
  34. 34.
    Kirmse W, Mrotzeck U, Siegfried R (1991) Chem Ber 124:241CrossRefGoogle Scholar
  35. 35.
    Bruker programs (2009) APEX2 version 2009.9-0, SAINT version 7.68 A, SADABS version 2008/1, SHELXTL version 2008/4. Bruker AXS Inc, MadisonGoogle Scholar
  36. 36.
    Sheldrick GM (2008) Acta Crystallogr A 64:112CrossRefGoogle Scholar
  37. 37.
    Lexer C, Burtscher D, Perner B, Tzur E, Lemcoff NG, Slugovc C (2011) J Organomet Chem 696:2466CrossRefGoogle Scholar
  38. 38.
    Riegler S, Demel S, Trimmel G, Slugovc C, Stelzer F (2006) J Mol Catal A 257:53CrossRefGoogle Scholar
  39. 39.
    Slugovc C, Demel S, Riegler S, Hobisch J, Stelzer F (2004) J Mol Catal A 213:107CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Anita Leitgeb
    • 1
  • Kurt Mereiter
    • 2
  • Christian Slugovc
    • 1
  1. 1.Institute for Chemistry and Technology of MaterialsGraz University of TechnologyGrazAustria
  2. 2.Institute of Chemical Technology and AnalyticsVienna University of TechnologyViennaAustria

Personalised recommendations