Skip to main content
SpringerLink
Log in

Transformations of Alkenes and Alkynes

  • Chapter
Organometallic Chemistry and Catalysis

  • 7562 Accesses

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 79.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 99.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Chapter 15-Transformations of alkenes and alkynes

  1. R.H. Grubbs Ed.-Handbook of Metathesis, Wiley-VCH, Weinheim, 2003, Vol. 1–3.

    Google Scholar 

  2. R.R. Schrock-Recent Advances In Olefin Metathesis by Molybdenum and Tungsten Imido Alkylidene Complexes, J. Mol. Cat. A: Chemical 213, 21, 2004.

    Article  CAS  Google Scholar 

  3. R.H. Grubbs-Olefin Metathesis, Tetrahedron 60, 7117, 2004; The Development of L2X2Ru=CHR Olefin Metathesis Catalysts: an Organometallic Success Story, Acc. Chem. Res. 34, 18, 2001.

    Article  CAS  Google Scholar 

  4. a) K.J. Ivin, J.C. Mol-Olefin Metathesis and Metathesis Polymerization, Academic Press, New York, 1997; b) T.J. Katz-The Olefin Metathesis Reaction, Adv. Organomet. Chem. 16, 283, 1977

    Google Scholar 

  5. D. Astruc-The Metathesis Reactions: from a Historical Perspective to Recent Developments, New J. Chem. 29, 42, 2005.

    Article  CAS  Google Scholar 

  6. R.L. Banks, G.C. Bailey-Ind. Eng. Chem., Prod. Res. Dev., 170, 1964; H.S. Eleuterio-Historical Account of the Early Days, J. Mol. Cat. 65, 55, 1991.

    Google Scholar 

  7. J.L. Hérisson, Y. Chauvin-Catalyse de transformation des oléfines par les complexes du tungstène: télomérisation des oléfines cycliques en présence d’oléfines acycliques, Macromol. Chem. 141, 161, 1971,.

    Article  Google Scholar 

  8. R.R. Schrock-Catalysis by Transition Metals: Metal-Carbon Double Bonds and Triple Bonds, Science 219, 13, 1983.

    Article  CAS  Google Scholar 

  9. R.R. Schrock et al.-J. Am. Chem. Soc. 102, 4515 and 6236, 1980; J. Mol. Cat. 8, 73, 1980.

    Article  Google Scholar 

  10. J. Kress, M. Welosek, J.A. Osborn-W(IV) Carbene for the Metathesis of Olefins. Direct Observation and Identification of the Chain Carrying Carbene Complexes in a Highly Active Catalyst System, J. Chem. Soc., Chem. Commun., 514, 1982; J. Am. Chem. Soc. 105, 6346, 1983.

    Google Scholar 

  11. a) P. Schwab, M.B. France, J.W. Ziller, R.H. Grubbs-A Series of Well-Defined Metathesis Catalysts-Synthesis of [RuCl2(=CHR’)(PR3)] and its Reactions, Angew. Chem. Int. Ed. Engl. 34, 2039, 1995; P. Schwab, R.H. Grubbs, J.W. Ziller J. Am. Chem. Soc. 118, 100, 1996; Ring-Closing Metathesis and Related Processes in Organic Synthesis, Acc. Chem. Res. 28, 446, 1995; b) M. Scholl, T.M. Trnka, J.P. Morgan, R.H. Grubbs-Tetrahedron Lett. 40, 2247, 1999; J. Huang, E.D. Stevens, S.P. Nolan, J.L. Petersen-J. Am. Chem. Soc. 121, 2647, 1999; L. Ackermann, A. Fürstner, T. Weskamp, F.J. Kohl, W.A. Herrmann Tetrahedron Lett. 40, 4787, 1999; M. Scholl, S. Ding, C.W. Lee, R.H. Grubbs-Org. Lett. 1, 953, 1999.

    Article  CAS  Google Scholar 

  12. A. Fürstner-Olefin Metathesis and Beyond, Angew. Chem. Int. Ed. 39, 3012, 2000.

    Article  Google Scholar 

  13. C. Dietrich-Bucherer, G. Rapenne, J.-P. Sauvage-Efficient Synthesis of a Molecular Knot by Copper(I)-Induced Formation of the Precursor Followed by Ruthenium(II)-Catalyzed Ring Closing Metathesis, Chem. Commun., 2053, 1997.

    Google Scholar 

  14. M. Schuster, S. Blechert-Angew. Chem. Int. Ed. 36, 2036, 1997; S.J. Connor, S. Blechert-Recent Developments in Olefin Cross-Metathesis, Angew. Chem. Int. Ed. 42, 1900, 2003.

    Article  Google Scholar 

  15. J.A. Gladysz et al.-Metal-catalyzed Olefin Metathesis in Metal Coordination Spheres, Chem. Eur. J. 7, 3931, 2001; in ref. 15.1, Vol. 2, 403; Angew. Chem. Int. Ed. 43, 5537, 2004.

    Article  Google Scholar 

  16. A.V. Chuchryukin, H.P. Dijkstra, B.M.J.M. Suijkerbuijk, R.J.M. Klein Gebbink, G.P.M. Van Klink, A.M. Mills, A.L. Spek, G. Van Koten-Macrocycle Synthesis by Olefin Metathesis on a Nanosized, Shape-Persistent Tricationic Platinum Template, Angew. Chem. Int. Ed. 42, 228, 2003.

    Article  Google Scholar 

  17. P. Wang, C.N. Moorefield, G.R. Newkome-Nanofabrication: Reversible Self-Assembly of an Imbedded Hexameric Metallomacrocycle within a Macromolecular Superstructure, Angew. Chem. Int. Ed. 44, 1679, 2005.

    Article  CAS  Google Scholar 

  18. N.G. Lemcoff, T.A. Spurlin, A.A. Gewirth, S.C. Zimmerman, J.B. Beil, S.L. Elmer, H.G. Vandeveer-Organic Nanoparticles Whose Size and Rigidity Are Finely Tuned by Cross-Linking the End Groups of Dendrimers, J. Am. Chem. Soc. 126, 11420, 2004; J. Beil, N.G. Lemcoff, S.C. Zimmerman-J. Am. Chem. Soc. 126, 13576, 2004.

    Article  CAS  Google Scholar 

  19. a) V. Martinez, J.-C. Blais, D. Astruc-A Fast Organometallic Route from p-Xylene, Mesitylene, and p-Diisopropylbenzene to Organoiron and Polycyclic Aromatic Cyclophanes, Capsules and Polymers, Angew. Chem. Int. Ed. 42, 4366, 2003; b) C. Ornelas, D. Méry, J.-C. Blais, E. Cloutet, J. Ruiz Aranzaes-Efficient Mono-and Bifunctionalization of Polyolefin Dendrimers by Metathesis, Angew. Chem. Int. Ed. 44, 7852, 2005.

    Article  CAS  Google Scholar 

  20. R.R. Schrock, A.H. Hoveyda-Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts, Angew. Chem. Int. Ed. 42, 4592, 2003.

    Article  CAS  Google Scholar 

  21. C. Coperet, F. Lefebvre, J.-M. Basset-Well-defined Metallocarbenes and Metallocarbynes Supported on Oxide Supports Prepared via Surface Organometallic Chemistry: a Source of Highly Active Alkane, Alkene and Alkyne Metathesis Catalysts, in ref. 15.1, Vol. 1, 33 and 190; J. Am. Chem. Soc. 123, 2062, 2001.

    Chapter  Google Scholar 

  22. A. Mortreux, M. Blanchard-Alkyne Metathesis Catayzed by Mo(CO)6 + Phenol. J. Chem. Soc., Chem. Commun., 786, 1974; A. Mortreux, F. Petit, M. Blanchard-13C Tracer Studies of Alkynes Metathesis, Tetrahedron Lett. 49, 4967, 1978.

    Google Scholar 

  23. M. Blanchard, A. Mortreux-J. Mol. Cat. 1, 101, 1975–6.

    Google Scholar 

  24. R.R. Schrock-Acc. Chem. Res. 19, 342, 1986; High Oxidation State Multiple Metal-Carbon Bonds, Chem. Rev. 102, 145, 2002; in ref. 15.1, Vol. 1, 173.

    Article  CAS  Google Scholar 

  25. K. Grela, J. Ignatowska-An Improved Catalyst for Ring-Closing Alkyne Metathesis Based on Molybdenum Hexacarbonyl/2-Fluorophenol, Org. Lett. 4, 3747, 2002.

    Article  CAS  Google Scholar 

  26. V. Huc, R. Weihofen, I. Martin-Jimenez, P. Oulié, C. Lepetit, G. Lavigne, R. Chauvin-Ether-Induced Rate Enhancement of Mo-Catalyzed Alkyne Metathesis Under Mild Conditions, New J. Chem. 27, 1412, 2003.

    Article  CAS  Google Scholar 

  27. U.H.F. Bunz-Acc. Chem. Res. 34, 998, 2001; in Modern Arene Chemistry, D. Astruc Ed., Wiley-VCH, Weinheim, 2002, 217.

    Article  CAS  Google Scholar 

  28. a) A. Fürstner, C. Mathes, C.W. Lehmann,-Mo[N(t-Bu)(Ar)]3 Complexes as Catalyst Precursors: In Situ Activation and Application to Metathesis Reactions of Alkynes and Diynes, J. Am. Chem. Soc. 121, 9453, 1999; in ref. 15.1, Vol. 2, 432; b) A. Mortreux, O. Coutelier-J. Mol. Cat. A: Chemical 254, 96, 2006.

    Article  Google Scholar 

  29. C. Cummins-Reductive Cleavage and Related Reactions Leading to Molybdenum-Element Multiple Bonds: New Pathways Offered by Three-Coordinate MoIII, Chem. Commun. 47, 1777, 1998; Prog. Inorg. Chem. 47, 685, 199.

    Article  Google Scholar 

  30. W. Zhang, S. Kraft, J.S. Moore-A Reductive Recycle Strategy for the Facile Synthesis of MoVI Alkylidyne Catalysts for Alkyne Metathesis, Chem. Commun., 832, 2003; J. Am. Chem. Soc. 126, 329, 2004.

    Google Scholar 

  31. R.R. Schrock-Living Ring-Opening Metathesis Polymerization Catalyzed by Well-Characterized Transition Metal Alkylidene Complexes, Acc. Chem. Res. 23, 158, 1990.

    Article  CAS  Google Scholar 

  32. R. H. Grubbs, W. Tumas-Polymer Synthesis and Organotransition Metal Chemistry, Science 243, 907, 1989.

    Article  CAS  Google Scholar 

  33. M.-H. Desbois, D. Astruc-Coupling Electron-Transfer Catalysis with Organometallic Catalysis: Carbenic Polymerization of Alkynes, New. J. Chem. 13, 595, 1989.

    CAS  Google Scholar 

  34. A. Bre, Y. Chauvin, D. Commereuc-Mode of Decomposition of Titanacyclopentane Complexes. Model of Intermediate Species in the Dimerization of Olefins Catalyzed by Titanium Complexes, Nouv. J. Chim. 10, 535, 1986.

    CAS  Google Scholar 

  35. Y. Chauvin, H. Olivier-Dimerization and Codimerization, in W.A. Herrmann Eds-Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1996 ref. 15.36a, Vol 1, Chap. 2.3.1.4, 258–268.

    Google Scholar 

  36. a) B. Cornils, W.A. Herrmann Eds-Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1996; b) in ref. 15.36a, Vol 1, Chap. 2.3.1-2.3.6.

    Google Scholar 

  37. R.R. Schrock, S. McLain, J. Sancho-Tantalacyclopentane Complexes and Their Role in the Catalytic Dimerization of Olefins, Pure Appl. Chem. 52, 729, 1980; J. Am. Chem. Soc. 101, 4558, 1979.

    Article  CAS  Google Scholar 

  38. R.H. Grubbs et al.-Metallacyclopentanes as Catalysts for the Linear and Cyclodimerization of Olefins, J. Am. Chem. Soc. 100, 7416, 1978.

    Article  CAS  Google Scholar 

  39. P. Braunstein, F. Naud-Hemilability oh Hybrid Ligands and the Coordination Chemistry of Oxazoline-Based Systems, Angew. Chem. Int. Ed. 40, 680, 2001.

    Article  CAS  Google Scholar 

Download references

Rights and permissions

Reprints and permissions

Copyright information

© 2007 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

(2007). Transformations of Alkenes and Alkynes. In: Organometallic Chemistry and Catalysis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-46129-6_18

Download citation

Publish with us

Policies and ethics

Search

Navigation