Catalytic dimerization reactions of α-olefuis and α,ω-dienes with Cp2ZrCl2/poly(methylalumoxane): Formation of dimers, carbocycles, and oligomers

Journal of the American Chemical Society

Volumn 118, Issue 19, 1996, Pages 4715-4716

  Christoffers, Jens ^a   Bergman, Robert G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE; POLYENE;

ARTICLE; CATALYSIS; DIMERIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029896197     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960227n     Document Type: Article

References (30)

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11. For examples of other catalytic systems useful for dimerizing alkenes, see: (a) Al-Jaraliah, A. M.; Anabtawl, J. A.; Siddiqui, M. A. B.; Aitani, A. M.; Al-sa'doun, A. W. Catalysis Today 1992, 14, 1. (b) A.-Sa'doun. A. W. Appl. Catal. A: Gen. 1993, 105, 1. (c) McLain, S. J., Sancho, J.; Schrock, R. R. J. Am. Chem. Soc. 1980, 102, 5610. (d) Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bercaw, J. E. Synlett 1990, 74 and references cited in these papers. We are grateful to Prof. Bercaw for calling our attention to ref (d).
12. For examples of other catalytic systems useful for dimerizing alkenes, see: (a) Al-Jaraliah, A. M.; Anabtawl, J. A.; Siddiqui, M. A. B.; Aitani, A. M.; Al-sa'doun, A. W. Catalysis Today 1992, 14, 1. (b) A.-Sa'doun. A. W. Appl. Catal. A: Gen. 1993, 105, 1. (c) McLain, S. J., Sancho, J.; Schrock, R. R. J. Am. Chem. Soc. 1980, 102, 5610. (d) Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bercaw, J. E. Synlett 1990, 74 and references cited in these papers. We are grateful to Prof. Bercaw for calling our attention to ref (d).
13. For examples of other catalytic systems useful for dimerizing alkenes, see: (a) Al-Jaraliah, A. M.; Anabtawl, J. A.; Siddiqui, M. A. B.; Aitani, A. M.; Al-sa'doun, A. W. Catalysis Today 1992, 14, 1. (b) A.-Sa'doun. A. W. Appl. Catal. A: Gen. 1993, 105, 1. (c) McLain, S. J., Sancho, J.; Schrock, R. R. J. Am. Chem. Soc. 1980, 102, 5610. (d) Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bercaw, J. E. Synlett 1990, 74 and references cited in these papers. We are grateful to Prof. Bercaw for calling our attention to ref (d).
14. For examples of other catalytic systems useful for dimerizing alkenes, see: (a) Al-Jaraliah, A. M.; Anabtawl, J. A.; Siddiqui, M. A. B.; Aitani, A. M.; Al-sa'doun, A. W. Catalysis Today 1992, 14, 1. (b) A.-Sa'doun. A. W. Appl. Catal. A: Gen. 1993, 105, 1. (c) McLain, S. J., Sancho, J.; Schrock, R. R. J. Am. Chem. Soc. 1980, 102, 5610. (d) Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bercaw, J. E. Synlett 1990, 74 and references cited in these papers. We are grateful to Prof. Bercaw for calling our attention to ref (d).
15. MAO (solution in toluene) was either purchased from Akzo Chemicals Inc , Chicago, or prepared following a literature procedure: Resconi, L.; Boss, S.; Abi, L. Macmmalecule.; 1990, 23, 4489.
16. 2a: Onopchenko, A ; Cupples, B. L.; Kresse, A. N. Ind. Eng. Chem. Prod, Res. Dev. 1983, 22, 182. 2b: Bestmann. H. J.; Rosel, P.; Vostrowsky, O. Liebigs Ann. Chem. 1979, 1189. 2c: Liu, H. Q.; Deffieux, A.; Sigwalt, P. Makromol. Chem. 1991, 192, 2111
17. 2a: Onopchenko, A ; Cupples, B. L.; Kresse, A. N. Ind. Eng. Chem. Prod, Res. Dev. 1983, 22, 182. 2b: Bestmann. H. J.; Rosel, P.; Vostrowsky, O. Liebigs Ann. Chem. 1979, 1189. 2c: Liu, H. Q.; Deffieux, A.; Sigwalt, P. Makromol. Chem. 1991, 192, 2111
18. 2a: Onopchenko, A ; Cupples, B. L.; Kresse, A. N. Ind. Eng. Chem. Prod, Res. Dev. 1983, 22, 182. 2b: Bestmann. H. J.; Rosel, P.; Vostrowsky, O. Liebigs Ann. Chem. 1979, 1189. 2c: Liu, H. Q.; Deffieux, A.; Sigwalt, P. Makromol. Chem. 1991, 192, 2111
19. 6 has been reported, see: Shaughnessy, K. H.; Waymouth, R. M. J. Am. Chem. Soc. 1995, 117, 5873.
20. There are only very few examples of a transition-metal catalyzed seven-membered ring formation Review: Dyker, G, Angen. Chem., Int. Ed. Engl. 1995, 34, 2223.
21. Echavarren, A. M.: Stille, J. K J. Am. Chem. Soc 1988, 110, 1537.
22. + signals for species up to mlz 880 (n = 8) can be observed.
23. We see no delectable amounts of cyclic products, which contrasts with observations made in the reactions of dienes with conventional ZiegSer-Natta systems, cf.: (a) Ruiz de Ballesteros, O.; Venditto, V.; Aunemma, F.; Guerra, G.; Resconi, L.; Waymouth, R. M.; Mogstad, A.-L Macromolecules 1995, 28, 2383. (b) Mitani, M.; Oouchi. K.; Hayakawa, M.; Yamada, T.; Mukaiyama, T Chem. Lett. 1995, 905. as well as with Scandium catalysts (ref 6d).
24. We see no delectable amounts of cyclic products, which contrasts with observations made in the reactions of dienes with conventional ZiegSer-Natta systems, cf.: (a) Ruiz de Ballesteros, O.; Venditto, V.; Aunemma, F.; Guerra, G.; Resconi, L.; Waymouth, R. M.; Mogstad, A.-L Macromolecules 1995, 28, 2383. (b) Mitani, M.; Oouchi. K.; Hayakawa, M.; Yamada, T.; Mukaiyama, T Chem. Lett. 1995, 905. as well as with Scandium catalysts (ref 6d).
25. There is only one precedent for a polymeric compound of similar constitution: (a) Vans, X.; Jia, L.; Marks, T. J. J. Am. Chem. Sac. 1993, 115, 3392. (b) Jia, L.,Yans, X.. Vans. S.; Marks, T J. J. Am. Chem. Soc. 1996, 118, 1547.
26. There is only one precedent for a polymeric compound of similar constitution: (a) Vans, X.; Jia, L.; Marks, T. J. J. Am. Chem. Sac. 1993, 115, 3392. (b) Jia, L.,Yans, X.. Vans. S.; Marks, T J. J. Am. Chem. Soc. 1996, 118, 1547.
27. 8
28. 3 complex and a C=C double bond, followed by β-elimination to give the catalyrically active Zr-H species.
29. 2 and MAO in 1;1 ratio, without alkene present, has been reported before, see: Cam, D.; Giannini. U. Makromol. Chem. 1992, 193, 1049
30. Jordan, R. F. J. Organomet. Chem. 1985, 294, 321.