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Making Modern Materials by the Metathesis Manipulation of a Monoterpene

Recent research from the research groups of Professors Marc Hillmyer and Thomas Hoye.

Shingo Kobayashi and Cheng Lu working in the labs of Professors Marc Hillmyer and Tom Hoye recently demonstrated the controlled polymerization of a cyclic diene prepared from the ring-closing metathesis (RCM) reaction of myrcene, a naturally occurring hydrocarbon produced by a variety of plants or by the rearrangement of pinene, the principal component of turpentine. The cyclic diene 3-methylenecyclopentene (2) was synthesized from myrcene (1) by means of RCM chemistry. The monomer 2 could be polymerized by chain polymerization techniques using radical, anionic, and cationic initiators. The polymerization of 2 proceeded in "living" fashion in both anionic and cationic polymerization systems and afforded polymers in quantitative yield with narrow molecular weight distributions and predictable molecular weights. Furthermore, the living cationic polymerization of 2 proceeded smoothly to afford regiopure polymers having thermal properties consistent with a stereoregular structure. The second product in this RCM reaction is isobutylene, a monomer that can be converted into butyl rubber. In principle, this chemistry will allow us the overall transformation of the starting material 1 into polymeric materials with perfect atom economy.

Basic research that underpins the development of new materials from renewable resources is the focus of the new Center for Sustainable Polymers at the University of Minnesota. This work was recently reported in the Journal of the American Chemical Society (J. Am. Chem. Soc. 2009, 131, 7960–7961).


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