CaltechAUTHORS
  A Caltech Library Service

Ruthenium Alkylidene Initiated Living Ring-Opening Metathesis Polymerization (ROMP) of 3-Substituted Cyclobutenes

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. https://resolver.caltech.edu/CaltechAUTHORS:20180719-153343500

[img] PDF (Text giving experimental procedures for the synthesis of compounds 3, 5, and 7−27 and tables of polymerization results for monomers 15 and 18 (13 pages)) - Supplemental Material
See Usage Policy.

821Kb

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20180719-153343500

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://dx.doi.org/10.1021/ma961780sDOIArticle
https://pubs.acs.org/doi/suppl/10.1021/ma961780sPublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
Issue or Number:12
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:03 Oct 2019 20:02

Repository Staff Only: item control page