Preparation of Polycyclooctyne by Ring-Opening Polymerization Employing D0 Tungsten and Molybdenum Alkylidyne Complexes

Macromolecules

Volumn 22, Issue 6, 1989, Pages 2569-2576

  Krouse, S A ^a   Schrock, R R ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS--METALLIC COMPOUNDS; MOLYBDENUM COMPOUNDS; MONOMERS--POLYMERIZATION; POLYMERIZATION--CATALYSTS; TUNGSTEN COMPOUNDS;

MOLYBDENUM ALKYLIDYNE COMPLEXES; POLYCYCLOOCTYNE; RING-OPENING POLYMERIZATION; TUNGSTEN ALKYLIDYNE COMPLEXES;

POLYMERS;

EID: 0024681742     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma00196a004     Document Type: Article

References (19)

1. Ivin, K. J. Olefin Metathesis; Academic Press: New York, 1983. (b) Dragutan, V.; Balaban, A. T.; Dimonie, M. Olefin Metathesis and Ring-Opening Polymerization of Cyclo-Olefins, 2nd ed.; Wiley Interscience: New York, 1985
2. Gilliom, L. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 733. (b) Kress, J.; Osborn, J.; Greene, R. M. E.; Ivin, K. J.; Rooney, J. J. J. Chem. Soc., Chem. Commun. 1985, 874. (c) Schrock, R. R.; Feldman, J.; Grubbs, R. H.; Cannizzo, L. Macromolecules 1987, 20, 1169. (d) Krouse, S. A.; Schrock, R. R. Macromolecules 1988, 21, 1885. (d) Wallace, K. C.; Liu, A. H.; Dewan, J. C.; Schrock, R. R. J. Am. Chem. Soc. 1988, 4110, 4964. (e) Cannizzo, L. F.; Grubbs, R. H. Macromolecules 1987, 20, 1488. (f) Cannizzo, L. F.; Grubbs, R. H. Macromolecules 1988, 21, 1961. (g) Murdzek, J. S.; Schrock, R. R. Macromolecules 1987, 20, 2640. (h) Kress, J.; Osborn, J. A.; Amir-Ebrahimi, V.; Ivin, J.; Rooney, J. J. J. Chem. Soc., Chem. Commun. 1988, 1164. (i) Kress, J.; Osborn, J.; Greene, R. M. E.; Ivin, K. J.; Rooney, J. J. J. Am. Chem. Soc. 1987, 109, 899
3. Schrock, R. R.; Freudenberger, J. H.; Listemann, M. L.; McCullough, L. G. J. Mol. Catal. 1985, 28, 1. (b) Churchill, M. R.; Ziller, J. W.; Freudenberger, J. H.; Schrock, R. R. Organometallics 1984, 3, 1554. (c) Freudenberger, J. H.; Schrock,R. R.; Churchill, M. R.; Rheingold, A. L.; Ziller, J. W. Organometallics 1984, 3, 1563. (d) McCullough, L. G.; Schrock, R. R.; Dewan, J. C.; Murdzek, J. S. J. Am. Chem. Soc. 1985, 107, 5987. (e) Schrock, R. R. Acc. Chem. Res. 1986, 19, 342
4. ΔH for hydrogenation of cyclooctyne is ~ 6 kcal mol-1larger than that for hydrogenation of 4-octyne.4b (b) Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969
5. Krouse, S. A.; Schrock, R. R. Macromolecules 1987, 20, 903
6. Listemann, M. L.; Schrock, R. R. Organometallics 1985, 4, 74. (b) Schrock, R. R.; Listemann, M. L.; Sturgeoff, L. G. J. Am. Chem. Soc. 1982. 104. 4291
7. Freudenberger, J. H.; Schrock, R. R. Organometallics 1985, 4, 1937
8. A sample of polyoctenamer was prepared from 200 equiv of cyclooctene with W(CH-t-Bu)(N-2,6-C6H3-i-Pr2)[OCMe-(CF3)2]2:8bDePue, R., unpublished results. See ref 8c-8e for related ring-opening polymerizations using this catalyst. (b) Schrock, R. R.; DePue, R.; Feldman, J.; Schaverien, C. J.; Dewan, J. C.; Liu, A. H. J. Am. Chem. Soc. 1988, 110, 1423. (c) Novak, B. M.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 960. (d) Swager, T. M.; Dougherty, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 2973. (e) Klavetter, F. L.; Grubbs, R. H. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 425
9. Brandup, J.; Immergut, E. H. Polymer Handbook; Wiley: New York, 1975
10. Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1976, 98, 2143
11. Jacobson, H.; Stockmayer, W. H. J. Chem. Phys. 1950, 18, 1600
12. Hoecker, H. Angew. Makromol. Chem. 1981, 100, 87
13. Listemann, M. L. Ph.D. Thesis, Massachusetts Institute of Technology, 1985
14. Chisholm, M. H.; Folting, K.; Hoffman, D. M.; Huffman, J. C. J. Am. Chem. Soc. 1984, 106, 6794
15. Freudenberger, J. H.; Schrock, R. R. Organometallics 1986, 5, 398
16. Cyclic oligomers of cycloheptene and cyclooctene recently have been prepared with a heterogeneous olefin metathesis catalyst (Re on alumina) under nonequilibrium conditions.16b(b) Warwel, S.; Kaetker, H.; Rauenbusch, C. Angew. Chem., Int. Ed. Engl. 1987, 26, 702
17. Brandsma, L.; Verkruiisse, H. D. Synthesis 1978, 4, 290
18. Dale, J.; Hubert, A. J.; King, G. S. D. J. Chem. Soc. 1963, 73–86
19. Walba, D. M.; Wand, M. D.; Wilkes, M. C. J. Org. Chem. 1980, 45, 2259–2261