Communication

Synthesis of A,B-Alternating Copolymers by Ring-Opening-Insertion-Metathesis Polymerization^†

Tae-Lim Choi

Arnold and Mabel Laboratories of Chemical Synthesis Division of Chemistry and Chemical Engineering California Institute of Technology MC 164-30, Pasadena, CA 91125 (USA) Fax: (+1) 626-564-9297

Search for more papers by this author

Isaac M. Rutenberg,

Isaac M. Rutenberg

Arnold and Mabel Laboratories of Chemical Synthesis Division of Chemistry and Chemical Engineering California Institute of Technology MC 164-30, Pasadena, CA 91125 (USA) Fax: (+1) 626-564-9297

Search for more papers by this author

Robert H. Grubbs Prof.,

Robert H. Grubbs Prof.

[email protected]

Arnold and Mabel Laboratories of Chemical Synthesis Division of Chemistry and Chemical Engineering California Institute of Technology MC 164-30, Pasadena, CA 91125 (USA) Fax: (+1) 626-564-9297

Search for more papers by this author

Tae-Lim Choi,

Tae-Lim Choi

Arnold and Mabel Laboratories of Chemical Synthesis Division of Chemistry and Chemical Engineering California Institute of Technology MC 164-30, Pasadena, CA 91125 (USA) Fax: (+1) 626-564-9297

Search for more papers by this author

Isaac M. Rutenberg,

Isaac M. Rutenberg

Arnold and Mabel Laboratories of Chemical Synthesis Division of Chemistry and Chemical Engineering California Institute of Technology MC 164-30, Pasadena, CA 91125 (USA) Fax: (+1) 626-564-9297

Search for more papers by this author

Robert H. Grubbs Prof.,

Robert H. Grubbs Prof.

[email protected]

Arnold and Mabel Laboratories of Chemical Synthesis Division of Chemistry and Chemical Engineering California Institute of Technology MC 164-30, Pasadena, CA 91125 (USA) Fax: (+1) 626-564-9297

Search for more papers by this author

First published: 18 October 2002

https://doi.org/10.1002/1521-3773(20021018)41:20<3839::AID-ANIE3839>3.0.CO;2-H

Citations: 116

^†

We thank the NIH and NSF for generous support of this research, and Dr. C. W. Lee, Dr. A. F. M. Kilbinger, Dr. J. P. Gallivan, O. A. Scherman, C. W. Bielawski, D. Benitez, and D. P. Sanders for helpful discussions.

Share a link

Email
Wechat
Bluesky

Graphical Abstract

A variety of highly A,B-alternating copolymers are formed from diacrylates and cycloalkenes in the presence of [Cl₂(PCy₃)(H₂IMes)RuCHPh] (1). The high conversion and the high selectivity come from the thermodynamically favored formation of a CC double bond between these monomers.

Supporting Information

References

1
1aG. Odian, Principles of Polymerizations, Wiley, New York, 1991;
Google Scholar
1bE. Drent, P. H. M. Budzelaar, Chem. Rev. 1996, 96, 663.
10.1021/cr940282j
CAS PubMed Web of Science® Google Scholar
2For recent reviews on ROMP, see:
Google Scholar
2aK. J. Ivin, J. C. Mol, Olefin Metathesis and Metathesis Polymerization, Academic Press, San Diego, 1997;
Google Scholar
2bR. H. Grubbs, E. Khosravi, Mater. Sci. Technol. 1999, 20, 65;
CAS Google Scholar
2cM. R. Buchmeiser, Chem. Rev. 2000, 100, 1565.
10.1021/cr990248a
CAS PubMed Web of Science® Google Scholar
3For a recent report using catalyst 3, see; S. E. Lehman, K. B. Wagener, Macromolecules 2002, 35, 48, and references therein.
10.1021/ma011094f
CAS Web of Science® Google Scholar
4
4aB. A. Samak, A. G. Carvill, J. G. Hamilton, J. J. Rooney, J. M. Thompson, Chem. Commun. 1997, 2057;
10.1039/a705046a
Web of Science® Google Scholar
4bB. A. Samak, V. Amir-Ebrahimi, D. G. Corry, J. G. Hamilton, S. Rigby, J. J. Rooney, J. M. Thompson, J. Mol. Catal. 2000, 160, 13;
10.1016/S1381-1169(00)00228-4
Web of Science® Google Scholar
4cM. F. Ilker, E. B. Coughlin, Macromolecules 2002, 35, 54.
10.1021/ma011394x
CAS Web of Science® Google Scholar
5R. R. Schrock, Acc. Chem. Res. 1990, 23, 158.
10.1021/ar00173a007
CAS Web of Science® Google Scholar
6P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100.
10.1021/ja952676d
CAS Web of Science® Google Scholar
7M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953.
10.1021/ol990909q
CAS PubMed Web of Science® Google Scholar
8
8aA. K. Chatterjee, R. H. Grubbs, Org. Lett. 1999, 1, 1751;
10.1021/ol991023p
CAS PubMed Web of Science® Google Scholar
8bA. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783;
10.1021/ja9939744
CAS Web of Science® Google Scholar
8cT.-L. Choi, A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2001, 113, 1317;
10.1002/1521-3757(20010401)113:7<1317::AID-ANGE1317>3.0.CO;2-X
Web of Science® Google Scholar
Angew. Chem. Int. Ed. 2001, 40, 1277;
10.1002/1521-3773(20010401)40:7<1277::AID-ANIE1277>3.0.CO;2-E
CAS PubMed Web of Science® Google Scholar
8dA. K. Chatterjee, T.-L. Choi, R. H. Grubbs, Synlett 2001, 1034;
10.1055/s-2001-14654
CAS Web of Science® Google Scholar
8eT.-L. Choi, R. H. Grubbs, Chem. Commun. 2001, 2648;
10.1039/b108306f
CAS Web of Science® Google Scholar
8fC. W. Lee, T.-L. Choi, R. H. Grubbs, J. Am. Chem. Soc. 2002, 124, 3224.
10.1021/ja017790c
CAS PubMed Web of Science® Google Scholar
9C. W. Bielawski, R. H. Grubbs, Angew. Chem. 2000, 112, 3025;
10.1002/1521-3757(20000818)112:16<3025::AID-ANGE3025>3.0.CO;2-F
Google Scholar
Angew. Chem. Int. Ed. 2000, 39, 2903.
10.1002/1521-3773(20000818)39:16<2903::AID-ANIE2903>3.0.CO;2-Q
CAS PubMed Web of Science® Google Scholar
10R. R. Schrock, K. B. Yap, D. C. Yang, H. Sitzmann, L. R. Sita, G. C. Bazan, Macromolecules 1989, 22, 3191.
10.1021/ma00198a001
CAS Web of Science® Google Scholar
11The number was obtained by AM1 calculation from Spartan v. 1.1, Wavefunction.
Google Scholar
12T.-L. Choi, C. W. Lee, A. K. Chatterjee, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 10 417.
10.1021/ja016386a
CAS PubMed Web of Science® Google Scholar

Citing Literature

Volume41, Issue20

October 18, 2002

Pages 3839-3841

This article also appears in:

In Celebration of Robert H. Grubbs

Synthesis of A,B-Alternating Copolymers by Ring-Opening-Insertion-Metathesis Polymerization^†

Graphical Abstract

Supporting Information

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Synthesis of A,B-Alternating Copolymers by Ring-Opening-Insertion-Metathesis Polymerization†

Graphical Abstract

Supporting Information

References

Citing Literature

References

Related

Information

Synthesis of A,B-Alternating Copolymers by Ring-Opening-Insertion-Metathesis Polymerization^†