Regio- and Stereoselective Ring-Opening Metathesis Polymerization of 3-Substituted Cyclooctenes

作者：Shingo Kobayashi, Louis M. Pitet, Marc A. Hillmyer · 发表于：Journal of the American Chemical Society · 年份：2011 · DOI：10.1021/ja201644v · 被引用次数：156 · 研究领域：Synthetic Organic Chemistry Methods、Model-Driven Software Engineering Techniques、Chemical Synthesis and Analysis

3-Substituted cis-cyclooctenes (3RCOEs, R = methyl, ethyl, hexyl, and phenyl) were synthesized and polymerized, and the polymers therefrom were hydrogenated to prepare model linear low density polyethylene (LLDPE) samples. The ring-opening metathesis polymerization (ROMP) of the 3RCOEs using Grubbs' catalyst proceeded in a regio- and stereoselective manner to afford polyoctenamers [poly(3RCOE)] exhibiting remarkably high head-to-tail regioregularity and high trans-stereoregularity. The overall selectivity increases with the increasing size of the R substituent. Hydrogenation of poly(3RCOE)s afforded precision LLDPEs with R substituents on every eighth backbone carbon.