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Published April 27, 2010 | Supplemental Material
Journal Article Open

Synthesis of Telechelic Polyisoprene via Ring-Opening Metathesis Polymerization in the Presence of Chain Transfer Agent


Telechelic polyisoprene was synthesized via the ring-opening metathesis polymerization (ROMP) of 1,5-dimethyl-1,5-cyclooctadiene (DMCOD) in the presence of cis-1,4-diacetoxy-2-butene as a chain transfer agent (CTA). This method afforded telechelic polymer in excellent yield, and the acetoxy groups were successfully removed to yield α,ω-hydroxy end-functionalized polyisoprene with potential for subsequent reactions. Efficient, quantitative incorporation of CTA was achieved, and NMR spectroscopy was utilized to confirm the chemical identity of the polymer end groups. Polymerization of discrete DMCOD monomer generated polyisoprene with excellent regioregularity in the polymer backbone. Successful ROMP of sterically challenging DMCOD in the presence of a CTA for chain end-functionalization was borne out through screening of a variety of Ru-based olefin metathesis catalysts.

Additional Information

© 2010 American Chemical Society. Received December 14, 2009; Revised Manuscript Received March 11, 2010. Publication Date (Web): March 30, 2010. The authors thank Wrigley Corporation and the National Science Foundation for providing funding. We thank Dr. John B.Matson for helpful discussions and Dr. David VanderVelde for assistance with NMR spectroscopy.

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Supplemental Material - ma902749q_si_001.pdf


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