{"id":200,"date":"2020-01-16T15:17:28","date_gmt":"2020-01-16T20:17:28","guid":{"rendered":"http:\/\/blog.richmond.edu\/downey\/?p=200"},"modified":"2020-01-16T15:17:28","modified_gmt":"2020-01-16T20:17:28","slug":"up-acetonitrile","status":"publish","type":"post","link":"https:\/\/blog.richmond.edu\/downey\/2020\/01\/16\/up-acetonitrile\/","title":{"rendered":"Up Acetonitrile!"},"content":{"rendered":"<p>Good news from here at the University of Richmond. \u00a0The excellent work of Grace Ann Robertson &#8217;21, Matt Santa &#8217;17, Kari Flicker &#8217;18, and William Stith &#8217;18 has produced a fine manuscript in <a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S004040391931336X?via%3Dihub\">Tetrahedron Letters<\/a>! \u00a0Matt and Will began this project one summer a few years ago, Kari carried it on, and Grace Ann finished it off in the summer of 2019. \u00a0I even contributed a little bit myself while Grace Ann was out of the country.<\/p>\n<p>We&#8217;ve developed a useful way of converting acetonitrile, when used in solvent quantities, into a mildly nucleophilic silyl ketene imine in the presence of TMSOTf and an amine base. \u00a0When either an acetal or a nitrone is present, a TMSOTf-promoted Mukaiyama-like reaction takes place to yield beta-methoxynitriles or beta-aminonitriles, depending on the electrophile. \u00a0The project grew out of some long-ago work with other nitriles by Carly Mueller &#8217;14, Alice Lee &#8217;16, and Jack Goodin &#8217;18. \u00a0Those were the days!<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Good news from here at the University of Richmond. \u00a0The excellent work of Grace Ann Robertson &#8217;21, Matt Santa &#8217;17, Kari Flicker &#8217;18, and William Stith &#8217;18 has produced a fine manuscript in Tetrahedron Letters! \u00a0Matt and Will began this<\/p>\n","protected":false},"author":2955,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-200","post","type-post","status-publish","format-standard","hentry","category-uncategorized"],"jetpack_featured_media_url":"","_links":{"self":[{"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/posts\/200","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/users\/2955"}],"replies":[{"embeddable":true,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/comments?post=200"}],"version-history":[{"count":0,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/posts\/200\/revisions"}],"wp:attachment":[{"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/media?parent=200"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/categories?post=200"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/tags?post=200"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}