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The diquat cations were obtained in high diastereo\u2010 and enantiomeric purity (<jats:italic>ee<\/jats:italic>&gt;96\u2009% in most cases). X\u2010ray diffraction analysis coupled with circular dichroism (CD) measurements allowed a precise determination of the relative and absolute configuration of the salts. The barriers to racemization of these compounds were calculated by using CD time\u2010course measurements at different temperatures, affording \u0394<jats:italic>G<\/jats:italic><jats:sup>\u2260<\/jats:sup> values above 25\u2005kcal\u2009mol<jats:sup>\u22121<\/jats:sup>. Derivatives <jats:bold>4\u2009a<\/jats:bold>, <jats:bold>4\u2009b<\/jats:bold>, and <jats:bold>4\u2009c<\/jats:bold> are the first eight\u2010membered\u2010ring derivatives with only three ring constraints to be resolved. This manuscript also reports the first procedure to remove TRISPHAT anions after diastereomeric separation.<\/jats:p>","DOI":"10.1002\/chem.200902562","type":"journal-article","created":{"date-parts":[[2010,1,22]],"date-time":"2010-01-22T13:17:59Z","timestamp":1264166279000},"page":"2797-2805","source":"Crossref","is-referenced-by-count":19,"title":["Resolution of the First Nonracemic Diquats"],"prefix":"10.1002","volume":"16","author":[{"given":"J\u00e9r\u00f4me","family":"Vachon","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"G\u00e9rald","family":"Bernardinelli","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J\u00e9r\u00f4me","family":"Lacour","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2010,2,19]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1038\/1842012b0"},{"key":"e_1_2_6_1_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja00295a013"},{"key":"e_1_2_6_1_4","doi-asserted-by":"publisher","DOI":"10.1021\/jo00255a015"},{"key":"e_1_2_6_1_5","doi-asserted-by":"publisher","DOI":"10.1021\/j100132a003"},{"key":"e_1_2_6_1_6","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2860(95)08938-R"},{"key":"e_1_2_6_1_7","doi-asserted-by":"publisher","DOI":"10.1055\/s-2005-921745"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9600002498"},{"volume-title":"The Bipyridinium Herbicides","year":"1980","author":"Summers L. 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