{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T01:08:02Z","timestamp":1759972082004,"version":"build-2065373602"},"reference-count":33,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2010,3,30]],"date-time":"2010-03-30T00:00:00Z","timestamp":1269907200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2010,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Attempts to use alkylation to introduce a positive charge at the nitrogen atom of the 4\u2010pyridyl ring in the bis(bidentate) triazole ligand <jats:italic>N<\/jats:italic><jats:sup>4<\/jats:sup>\u2010(4\u2010pyridyl)\u20103,5\u2010di(2\u2010pyridyl)\u20101,2,4\u2010triazole (<jats:bold>pydpt<\/jats:bold>) were made to ascertain what effect a strongly electron\u2010withdrawing group would have on the magnetic properties of any subsequent iron(II) complexes. Alkylation of <jats:bold>pydpt<\/jats:bold> under relatively mild conditions led in some cases to unexpected rearrangement products. Specifically, when benzyl bromide is used as the alkylating agent, and the reaction is carried out in refluxing acetonitrile, the <jats:italic>N<\/jats:italic><jats:sup>4<\/jats:sup> substituent moves to the <jats:italic>N<\/jats:italic><jats:sup>1<\/jats:sup>\u2005position. However, when the same reaction is performed in dichloromethane at room temperature, the rearrangement does not occur and the desired product containing an alkylated <jats:italic>N<\/jats:italic><jats:sup>4<\/jats:sup> substituent is obtained. Heating a pure sample of <jats:italic>N<\/jats:italic><jats:sup>4<\/jats:sup>\u2010Bzpydpt\u22c5Br to reflux in MeCN resulted in clean conversion to <jats:bold>N1Bzpydpt.Br<\/jats:bold>. This is consistent with <jats:bold>N4\u2010Bzpydpt.Br<\/jats:bold> being the kinetic product whereas <jats:bold>N1Bzpydpt.Br<\/jats:bold> is the thermodynamic product. When methyl iodide is used as the alkylating agent, the <jats:italic>N<\/jats:italic><jats:sup>4<\/jats:sup> to <jats:italic>N<\/jats:italic><jats:sup>1<\/jats:sup> rearrangement occurs even at room temperature, and at reflux <jats:bold>pydpt<\/jats:bold> is doubly alkylated. The observation of the lowest reported temperatures for an <jats:italic>N<\/jats:italic><jats:sup>4<\/jats:sup> to <jats:italic>N<\/jats:italic><jats:sup>1<\/jats:sup> rearrangement is due to this particular rearrangement involving nucleophilic aromatic substitution: a possible mechanism for this transformation is suggested.<\/jats:p>","DOI":"10.1002\/asia.200900485","type":"journal-article","created":{"date-parts":[[2010,3,12]],"date-time":"2010-03-12T04:48:52Z","timestamp":1268369332000},"page":"910-918","source":"Crossref","is-referenced-by-count":7,"title":["Alkylations of <i>N<\/i><sup>4<\/sup>\u2010(4\u2010Pyridyl)\u20103,5\u2010di(2\u2010pyridyl)\u20101,2,4\u2010triazole: First Observation of Room\u2010Temperature Rearrangement of an <i>N<\/i><sup>4<\/sup>\u2010Substituted Triazole to the <i>N<\/i><sup>1<\/sup> Analogue"],"prefix":"10.1002","volume":"5","author":[{"given":"Jonathan\u2005A.","family":"Kitchen","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"David\u2005S.","family":"Larsen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sally","family":"Brooker","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2010,3,30]]},"reference":[{"doi-asserted-by":"publisher","key":"e_1_2_6_1_2","DOI":"10.1021\/ja943960s"},{"doi-asserted-by":"publisher","key":"e_1_2_6_1_3","DOI":"10.1016\/S0020-1693(97)05954-9"},{"doi-asserted-by":"publisher","key":"e_1_2_6_1_4","DOI":"10.1016\/S0020-1693(99)00128-0"},{"doi-asserted-by":"publisher","key":"e_1_2_6_1_5","DOI":"10.1021\/ic0100976"},{"doi-asserted-by":"publisher","key":"e_1_2_6_1_6","DOI":"10.1021\/cm010688u"},{"doi-asserted-by":"publisher","key":"e_1_2_6_1_7","DOI":"10.1021\/ic034450e"},{"doi-asserted-by":"publisher","key":"e_1_2_6_2_2","DOI":"10.1016\/j.ccr.2007.11.010"},{"doi-asserted-by":"publisher","key":"e_1_2_6_3_2","DOI":"10.1021\/ic900634t"},{"unstructured":"J.\u2005A. 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