{"id":1672,"date":"2025-12-23T09:10:49","date_gmt":"2025-12-23T09:10:49","guid":{"rendered":"https:\/\/citations.tools.bio-logic.fr\/?p=1672"},"modified":"2025-12-23T09:10:49","modified_gmt":"2025-12-23T09:10:49","slug":"synthesis-structural-elucidation-cyclic-voltammetry-and-theoretical-modelling-of-2%e2%80%90ferrocenyl%e2%80%904h%e2%80%90benzoe13thiazines-and-2%e2%80%90aryl%e2%80%904h%e2%80%90ferrocenoe1","status":"publish","type":"post","link":"https:\/\/citations.tools.bio-logic.fr\/?p=1672","title":{"rendered":"Synthesis, Structural Elucidation, Cyclic Voltammetry, and Theoretical Modelling of 2\u2010Ferrocenyl\u20104<i>H<\/i>\u2010benzo[<i>e<\/i>][1,3]thiazines and 2\u2010Aryl\u20104<i>H<\/i>\u2010ferroceno[<i>e<\/i>][1,3]thiazines"},"content":{"rendered":"<h4>DOI:<\/h4>\n<p><a href=\"https:\/\/doi.org\/10.1002\/ejic.201601037\" target=\"_blank\" rel=\"noopener\">10.1002\/ejic.201601037<\/a><\/p>\n<h4>Authors:<\/h4>\n<p>Kinga Judit Fodor, Krist\u00f3f Heged\u00fcs, P\u00e9ter Csom\u00f3s, Lajos Fodor, Dorottya Gub\u00e1n, P\u00e0l Soh\u00e1r, Antal Cs\u00e1mpai<\/p>\n<h4>Abstract:<\/h4>\n<p>2\u2010Ferrocenyl\u20104 H \u2010benzo[ e ][1,3]thiazine and its 6,7\u2010dimethoxy derivative were prepared by a Bischler\u2013Napieralski\u2010type annulation of the Mannich adducts of ferrocenecarboxamide, formaldehyde, and the corresponding thiophenol. A more efficient synthetic pathway, comprising a directed lithiation\/iodination sequence followed by standard functional\u2010group transformations and a final copper\u2010catalyzed cyclization, was elaborated to convert [(dimethylamino)methyl]ferrocene into racemic mixtures of the first representatives of planar\u2010chiral 4 H \u2010ferroceno[ e ][1,3]thiazines. A similar strategy with 2\u2010iodobenzyl bromide as the precursor enabled a highly improved synthesis of 2\u2010ferrocenyl\u20104 H \u2010benzo[ e ][1,3]thiazine. The relative tendency of the new ferrocene\u2010based thiazines, composed of potential redox sites assembled in different molecular architectures, to behave as donors in single\u2010electron transfer (SET) reactions was studied by cyclic voltammetry (CV) and DFT calculations. The results disclosed that 2\u2010ferrocenyl\u20104 H \u2010ferroceno[ e ][1,3]thiazine can undergo two consecutive redox steps and is the most efficient reductant among the prepared models; it has the lowest first half\u2010cell potential, the highest\u2010energy highest occupied molecular orbital (HOMO) concentrated on the fused metallocene unit and the lowest first ionization energy.<\/p>\n","protected":false},"excerpt":{"rendered":"<h4>DOI:<\/h4>\n<div class=\"b-doi\">10.1002\/ejic.201601037<\/div>\n<h4>Authors:<\/h4>\n<div class=\"b-author\">Kinga Judit Fodor, Krist\u00f3f Heged\u00fcs, P\u00e9ter Csom\u00f3s, Lajos Fodor, Dorottya Gub\u00e1n, P\u00e0l Soh\u00e1r, Antal Cs\u00e1mpai<\/div>\n<h4>Abstract:<\/h4>\n<div class=\"b-intro\">2\u2010Ferrocenyl\u20104 H \u2010benzo[ e ][1,3]thiazine and its 6,7\u2010dimethoxy derivative were prepared by a Bischler\u2013Napieralski\u2010type annulation of the Mannich adducts of ferrocenecarboxamide, formaldehyde, and the corresponding thiophenol. A more efficient synthetic pathway, comprising a directed lithiation\/iodination sequence followed by standard functional\u2010group transformations and a final copper\u2010catalyzed cyclization, was elaborated to convert&hellip;<\/div>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[25],"tags":[],"class_list":["post-1672","post","type-post","status-publish","format-standard","hentry","category-sp-150-potentiostat"],"_links":{"self":[{"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=\/wp\/v2\/posts\/1672","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=1672"}],"version-history":[{"count":0,"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=\/wp\/v2\/posts\/1672\/revisions"}],"wp:attachment":[{"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=1672"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=1672"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/citations.tools.bio-logic.fr\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=1672"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}