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Unfortunately, straightforward methods for realizing high levels of stereocontrolled polymerizations are often challenging to achieve. In a departure from traditional metal\u2010mediated ring\u2010opening metathesis polymerization (ROMP), we discovered a remarkably simple method for controlling alkene stereochemistry in photoredox mediated metal\u2010free ROMP. Ion\u2010pairing, initiator sterics, and solvation effects each had profound impact on the stereochemistry of polynorbornene (PNB). Simple modifications to the reaction conditions produced PNB with\n                    <jats:italic>trans<\/jats:italic>\n                    alkene content of 25 to &gt;98\u2009%. High\n                    <jats:italic>cis<\/jats:italic>\n                    content was obtained from relatively larger counterions, toluene as solvent, low temperatures (\u221278\u2009\u00b0C), and initiators with low Charton values. Conversely, smaller counterions, dichloromethane as solvent, and enol ethers with higher Charton values enabled production of PNB with high\n                    <jats:italic>trans<\/jats:italic>\n                    content. Data from a combined experimental and computational investigation are consistent with the stereocontrolling step of the radical cationic mechanism proceeding under thermodynamic control.\n                  <\/jats:p>","DOI":"10.1002\/anie.202016393","type":"journal-article","created":{"date-parts":[[2021,3,15]],"date-time":"2021-03-15T23:17:19Z","timestamp":1615850239000},"page":"13952-13958","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["An Ion\u2010Pairing Approach to Stereoselective Metal\u2010Free Ring\u2010Opening Metathesis Polymerization"],"prefix":"10.1002","volume":"60","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4051-8579","authenticated-orcid":false,"given":"Xuejin","family":"Yang","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Wisconsin-Madison  Madison WI 53706 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