Maughon, Bob R. and Grubbs, Robert H. (1997) Ruthenium Alkylidene Initiated Living Ring-Opening Metathesis Polymerization (ROMP) of 3-Substituted Cyclobutenes. Macromolecules, 30 (12). pp. 3459-3469. ISSN 0024-9297. doi:10.1021/ma961780s. https://resolver.caltech.edu/CaltechAUTHORS:20180719-153343500
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Abstract
The synthesis and living ring-opening metathesis polymerization (ROMP) of substituted cyclobutenes were investigated with the functional group tolerant initiators (PCy_3)_2Cl_2Ru=CHCHCPh_2 (1) and (PCy_3)_2Cl_2Ru=CHPh (2). Synthetic methodology was developed for the synthesis of a wide variety of 3-functionalized cyclobutenes containing ether, ester, alcohol, amine, amide, and carboxylic acid substituents. Coordination of these functional groups to the propagating carbene was observed, resulting in the formation of a chelated propagating species with concomitant loss of one phosphine ligand from the metal center. Studies aimed at understanding this chelation and its effect on the polymerization were undertaken. On the basis of these results, the synthesis of a series of functionalized cyclobutenes was accomplished which minimized this chelation and allowed for living polymerizations. A new class of functionalized poly(butadiene)s were synthesized and their thermal properties analyzed by thermogravimetric analysis and differential scanning calorimetry.
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| Additional Information: | © 1997 American Chemical Society. Received December 4, 1996; Revised Manuscript Received March 25, 1997. This research has been funded by the National Science Foundation. We thank Dr. Peter Schwab for supplying the ruthenium catalyst and Eric Dias for many helpful discussions without which this research would not have been possible. | |||||||||
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| Issue or Number: | 12 | |||||||||
| DOI: | 10.1021/ma961780s | |||||||||
| Record Number: | CaltechAUTHORS:20180719-153343500 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20180719-153343500 | |||||||||
| Official Citation: | Ruthenium Alkylidene Initiated Living Ring-Opening Metathesis Polymerization (ROMP) of 3-Substituted Cyclobutenes Bob R. Maughon and Robert H. Grubbs Macromolecules 1997 30 (12), 3459-3469 DOI: 10.1021/ma961780s | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 88030 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | George Porter | |||||||||
| Deposited On: | 19 Jul 2018 22:45 | |||||||||
| Last Modified: | 16 Nov 2021 00:23 |
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