Double coordination and activation ability of methylalumoxane (MAO) for hetero functionality: Pivotal role as polymerization cocatalyst

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5365-5368

  Hanawa, Hideo ^a   Abe, Noriko ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALUMINUM DERIVATIVE; CARBONYL DERIVATIVE; METHYLALUMOXANE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; LIGAND BINDING; POLYMERIZATION; REACTION ANALYSIS;

EID: 0033575498     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01024-2     Document Type: Article

References (29)

1. Sinn, H.; Kaminsky, W. Adv. Organomet. Chem. 1980, 18, 99.
2. Kaminsky, W.; Arndt, M. Applied Homogeneous Catalysis with Organometallic Compounds, "Vol 1, Cornils, B., Herrmann, W. A. Eds., VCH, Weingeim, p 220 (1996).
3. For recent reviews, see: (a) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 225. (b) Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 1143. (c) Kaminsky, W. Catal. Today 1994, 20, 257. (d) Mohring, R. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1. (e) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (f) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
4. For recent reviews, see: (a) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 225. (b) Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 1143. (c) Kaminsky, W. Catal. Today 1994, 20, 257. (d) Mohring, R. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1. (e) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (f) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
5. For recent reviews, see: (a) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 225. (b) Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 1143. (c) Kaminsky, W. Catal. Today 1994, 20, 257. (d) Mohring, R. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1. (e) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (f) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
6. For recent reviews, see: (a) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 225. (b) Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 1143. (c) Kaminsky, W. Catal. Today 1994, 20, 257. (d) Mohring, R. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1. (e) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (f) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
7. For recent reviews, see: (a) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 225. (b) Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 1143. (c) Kaminsky, W. Catal. Today 1994, 20, 257. (d) Mohring, R. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1. (e) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (f) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
8. For recent reviews, see: (a) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 225. (b) Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 1143. (c) Kaminsky, W. Catal. Today 1994, 20, 257. (d) Mohring, R. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1. (e) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (f) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
9. (a) Imhoff, D. W.; Simeral, L. S.; Sangokoya, S. A.; Peel, J. H. Organometallics 1998, 17, 1941. (b) Harlan, C. J.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1995, 117, 6465. (c) Ziegler Catalysts; Fink, G., Mulhaupt, R., Brintzinger, H. H., Eds.; Springer: Berlin, 1995. (d) Transition Metals and Organometallics as Catalysts for Olefin Polymerization; Kaminsky, W., Sinn, H., Eds.; Springer: Berlin, 1988.
10. (a) Imhoff, D. W.; Simeral, L. S.; Sangokoya, S. A.; Peel, J. H. Organometallics 1998, 17, 1941. (b) Harlan, C. J.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1995, 117, 6465. (c) Ziegler Catalysts; Fink, G., Mulhaupt, R., Brintzinger, H. H., Eds.; Springer: Berlin, 1995. (d) Transition Metals and Organometallics as Catalysts for Olefin Polymerization; Kaminsky, W., Sinn, H., Eds.; Springer: Berlin, 1988.
11. (a) Imhoff, D. W.; Simeral, L. S.; Sangokoya, S. A.; Peel, J. H. Organometallics 1998, 17, 1941. (b) Harlan, C. J.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1995, 117, 6465. (c) Ziegler Catalysts; Fink, G., Mulhaupt, R., Brintzinger, H. H., Eds.; Springer: Berlin, 1995. (d) Transition Metals and Organometallics as Catalysts for Olefin Polymerization; Kaminsky, W., Sinn, H., Eds.; Springer: Berlin, 1988.
12. (a) Imhoff, D. W.; Simeral, L. S.; Sangokoya, S. A.; Peel, J. H. Organometallics 1998, 17, 1941. (b) Harlan, C. J.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1995, 117, 6465. (c) Ziegler Catalysts; Fink, G., Mulhaupt, R., Brintzinger, H. H., Eds.; Springer: Berlin, 1995. (d) Transition Metals and Organometallics as Catalysts for Olefin Polymerization; Kaminsky, W., Sinn, H., Eds.; Springer: Berlin, 1988.
13. (a) Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. (b) Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem. Int. Ed. Engl. 1998, 37, 2347. (c) Ooi, T.; Saito, A.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3745. (d) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307.
14. (a) Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. (b) Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem. Int. Ed. Engl. 1998, 37, 2347. (c) Ooi, T.; Saito, A.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3745. (d) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307.
15. (a) Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. (b) Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem. Int. Ed. Engl. 1998, 37, 2347. (c) Ooi, T.; Saito, A.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3745. (d) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307.
16. (a) Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729. (b) Ooi, T.; Miura, T.; Maruoka, K. Angew. Chem. Int. Ed. Engl. 1998, 37, 2347. (c) Ooi, T.; Saito, A.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3745. (d) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307.
17. 8. See: Imhoff, D. W.; Simeral, L. S.; Sangokoya, S. A.; Peel, J. H. Organometallics 1998, 17, 1941.
18. (a) Ueyama, N.; Araki, T.; Tani, H. Macromolecules 1974, 7, 153. (b) Ueyama, N.; Araki, T.; Tani, H. Inorg. Chem. 1973, 12, 2218.
19. (a) Ueyama, N.; Araki, T.; Tani, H. Macromolecules 1974, 7, 153. (b) Ueyama, N.; Araki, T.; Tani, H. Inorg. Chem. 1973, 12, 2218.
20. Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1982, 21, 96.
21. i to the complex (A) did not cause any noticeable shift for the DMF carbonyl.
22. 2O in the 1:2 mixture, while the double coordination complex (C) still predominates in the 2:1 mixture.
23. Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031. See also: Yamanoi, S.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1998, 39, 9727; 1999, 40, 2793.
24. Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031. See also: Yamanoi, S.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1998, 39, 9727; 1999, 40, 2793.
25. Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031. See also:Yamanoi, S.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1998, 39, 9727; 1999, 40, 2793.
26. For another synthetic application of MAO, see: Akakura, M.; Yamamoto, H. Synlett 1997, 277.
27. A similar tendency is also observed with several MAO analogues by Suzuki et.al. (Yamanoi, S.; Matsumoto, T.; Suzuki, K., private communication).
28. 2 solvents by vacuum evaporation. Attempted reaction of the compound 7, thus prepared, with 6-dodecyne and MAO (2 equiv in Al unit) under similar conditions gave allylation product 5 in 47% yield.
29. For a recent, related example, see: Kohler, K.; Piers, W. E.; Jarvis, A. P.; Xin, S.; Feng, Y.; Bravakis, A. M.; Collins, S.; Clegg, W.; Yap, G. P. A.; Marder, T. B. Organometallics 1998, 17, 3557.