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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

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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.

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References

  1. Grubbs RH (2003) Handbook of metathesis, vol 1–3. Wiley, Weinheim

    Book  Google Scholar 

  2. Trnka TM, Grubbs RH (2001) Acc Chem Res 34:18

    Article  CAS  Google Scholar 

  3. Burtscher D, Grela K (2009) Angew Chem Int Ed 48:442

    Article  CAS  Google Scholar 

  4. Hansen SM, Rominger F, Metz M, Hofmann P (1995) Chem Eur J 5:557

    Article  Google Scholar 

  5. Hansen SM, Volland MAO, Rominger F, Eisenträger F, Hofmann P (1999) Angew Chem Int Ed 38:1273

    Article  CAS  Google Scholar 

  6. Prühs S, Lehmann CW, Fürstner A (2004) Organometallics 23:280

    Article  Google Scholar 

  7. Slugovc C, Perner B, Stelzer F, Mereiter K (2004) Organometallics 23:3622

    Article  CAS  Google Scholar 

  8. Amoroso D, Jabri A, Yap GPA, Gusev DG, dos Santos EN, Fogg DE (2004) Organometallics 23:4047

    Article  CAS  Google Scholar 

  9. Ung T, Hejl A, Grubbs RH, Schrodi Y (2004) Organometallics 23:5399

    Article  CAS  Google Scholar 

  10. Barbasiewicz M, Szadkowska A, Bujok R, Grela K (2006) Organometallics 25:3599

    Article  CAS  Google Scholar 

  11. Gstrein X, Burtscher D, Szadkowska A, Barbasiewicz M, Stelzer F, Grela K, Slugovc C (2007) J Polym Sci Part A Polym Chem 45:3494

    Article  CAS  Google Scholar 

  12. Ben-Asuly A, Tzur E, Diesendruck CE, Sigalov M, Goldberg I, Lemcoff NG (2008) Organometallics 27:811

    Article  CAS  Google Scholar 

  13. Diesendruck CE, Vidavsky Y, Ben-Asuly A, Lemcoff NG (2009) J Polym Sci Part A Polym Chem 47:4209

    Article  CAS  Google Scholar 

  14. Bantreil X, Schmid TE, Randall RAM, Slawin AMZ, Cazin CSJ (2010) Chem Commun 46:7115

    Article  CAS  Google Scholar 

  15. Leitgeb A, Wappel J, Slugovc C (2010) Polymer 51:2927

    Article  CAS  Google Scholar 

  16. Leitgeb A, Szadkowska A, Michalak M, Barbasiewicz M, Grela K, Slugovc C (2011) J Polym Sci Part A Polym Chem 49:3448

    Article  CAS  Google Scholar 

  17. Monsaert S, Lozano Vila A, Drozdzak R, Voort Van Der P, Verpoort F (2009) Chem Soc Rev 38:3360

    Article  CAS  Google Scholar 

  18. Vidavsky Y, Anaby A, Lemcoff NG (2012) Dalton Trans 41:32

    Article  CAS  Google Scholar 

  19. Abbas M, Slugovc C (2011) Tetrahedron Lett 52:2560

    Article  CAS  Google Scholar 

  20. Abbas M, Slugovc C (2012) Monatsh Chem. doi:10.1007/s00706-011-0717-x

    Google Scholar 

  21. Ben-Asuly A, Aharoni A, Diesendruck CE, Vidavsky Y, Goldberg I, Straub BF, Lemcoff NG (2009) Organometallics 28:4652

    Article  CAS  Google Scholar 

  22. Benitez D, Tkatchouk E, Goddard WA III (2008) Chem Commun 46:6194–6196

    Article  Google Scholar 

  23. Poater A, Ragone F, Correa A, Szadkowska A, Barbasiewicz M, Grela K, Cavallo L (2010) Chem Eur J 16:14354

    Article  CAS  Google Scholar 

  24. Benitez D, Goddard WA III (2005) J Am Chem Soc 127:12218

    Article  CAS  Google Scholar 

  25. Zirngast M, Pump E, Leitgeb A, Albering JH, Slugovc C (2011) Chem Commun 47:2261

    Article  CAS  Google Scholar 

  26. Kattnig E, Albert M (2004) Org Lett 6:945

    Article  CAS  Google Scholar 

  27. Kerins F, O’Sheah DF (2002) J Org Chem 67:4968

    Article  CAS  Google Scholar 

  28. Garber SB, Kingsbury JS, Gray LB, Hoveyda AH (2000) J Am Chem Soc 122:8169

    Article  Google Scholar 

  29. Aharoni A, Vidavsky Y, Diesendruck CE, Ben-Asuly A, Goldberg I, Lemcoff NG (2011) Organometallics 30:1607

    Article  CAS  Google Scholar 

  30. Fürstner A, Thiel OR, Lehmann CW (2002) Organometallics 21:331

    Article  Google Scholar 

  31. Hong SH, Sanders DP, Lee CW, Grubbs RH (2005) J Am Chem Soc 127:17160

    Article  CAS  Google Scholar 

  32. Burtscher D, Lexer C, Mereiter K, Winde R, Karch R, Slugovc C (2008) J Polym Sci Part A Polym Chem 46:4630

    Article  CAS  Google Scholar 

  33. Urbina-Blanco CA, Manzini S, Pérez Gomes J, Doppiu A, Nolan SP (2011) Chem Commun 47:5022

    Article  CAS  Google Scholar 

  34. Kirmse W, Mrotzeck U, Siegfried R (1991) Chem Ber 124:241

    Article  CAS  Google Scholar 

  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, Madison

  36. Sheldrick GM (2008) Acta Crystallogr A 64:112

    Article  Google Scholar 

  37. Lexer C, Burtscher D, Perner B, Tzur E, Lemcoff NG, Slugovc C (2011) J Organomet Chem 696:2466

    Article  CAS  Google Scholar 

  38. Riegler S, Demel S, Trimmel G, Slugovc C, Stelzer F (2006) J Mol Catal A 257:53

    Article  CAS  Google Scholar 

  39. Slugovc C, Demel S, Riegler S, Hobisch J, Stelzer F (2004) J Mol Catal A 213:107

    Article  CAS  Google Scholar 

Download references

Acknowledgments

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

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Correspondence to Christian Slugovc.

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Leitgeb, A., Mereiter, K. & Slugovc, C. 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. Monatsh Chem 143, 901–908 (2012). https://doi.org/10.1007/s00706-012-0740-6

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  • DOI: https://doi.org/10.1007/s00706-012-0740-6

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