{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T14:23:16Z","timestamp":1761488596070,"version":"build-2065373602"},"reference-count":37,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2010,12,9]],"date-time":"2010-12-09T00:00:00Z","timestamp":1291852800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Inorg Chem"],"published-print":{"date-parts":[[2011,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Treatment of benzonitriles 4\u2010XC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>CN (<jats:bold>1<\/jats:bold>) [X = H (<jats:bold>1a<\/jats:bold>), F (<jats:bold>1b<\/jats:bold>), Cl (<jats:bold>1c<\/jats:bold>), Br (<jats:bold>1d<\/jats:bold>), I (<jats:bold>1e<\/jats:bold>)] with an excess of 2\u2010butanone oxime (Me)(Et)C=NOH (as a reagent and solvent) in the presence of PdCl<jats:sub>2<\/jats:sub> at 100 \u00b0C for 12 h affords the symmetrical cationic 2,4\u2010diaryl\u20101,3,5\u2010triazapentadiene (Htap) palladium(II) complexes [Pd(Htap)<jats:sub>2<\/jats:sub>]Cl<jats:sub>2<\/jats:sub> (<jats:bold>2\u2032<\/jats:bold>) [Htap = HN=C(4\u2010XC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>)NHC(4\u2010XC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>)=NH]. Recrystallization of <jats:bold>2\u2032<\/jats:bold> from MeOH\/CHCl<jats:sub>3<\/jats:sub> with two equivalents of <jats:italic>n<\/jats:italic>\u2010propylamine gives the corresponding neutral triazapentadienate (tap) complexes [Pd(tap)<jats:sub>2<\/jats:sub>] (<jats:bold>2<\/jats:bold>) [tap = HN=C(4\u2010XC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>)NC(4\u2010XC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>)=NH; X = H (<jats:bold>2a<\/jats:bold>), F (<jats:bold>2b<\/jats:bold>), Cl (<jats:bold>2c<\/jats:bold>), Br (<jats:bold>2d<\/jats:bold>), I (<jats:bold>2e<\/jats:bold>)] in good yields. When cyanoguanidine, HN=C(NH<jats:sub>2<\/jats:sub>)N(H)C\u2261N (<jats:bold>3<\/jats:bold>), or sodium dicyanamide NaN(C\u2261N)<jats:sub>2<\/jats:sub> (<jats:bold>5<\/jats:bold>) are treated with an excess of primary alcohols, ROH [R = Me, Et, <jats:italic>n<\/jats:italic>Pr, <jats:italic>n<\/jats:italic>Bu or (CH<jats:sub>2<\/jats:sub>)<jats:sub>2<\/jats:sub>OMe] in the presence of PdCl<jats:sub>2<\/jats:sub>, while being heated for 12 h, the corresponding asymmetrical 2\u2010amino\u20104\u2010alkoxy\u20101,3,5\u2010triazapentadienate\u2010Pd<jats:sup>II<\/jats:sup> complexes [Pd{HN=C(NH<jats:sub>2<\/jats:sub>)NC(OR)=NH}<jats:sub>2<\/jats:sub>] (<jats:bold>4<\/jats:bold>) [R = Me (<jats:bold>4a<\/jats:bold>), Et (<jats:bold>4b<\/jats:bold>), <jats:italic>n<\/jats:italic>Pr (<jats:bold>4c<\/jats:bold>), <jats:italic>n<\/jats:italic>Bu (<jats:bold>4d<\/jats:bold>)] or the symmetrical 2,4\u2010dialkoxy\u20101,3,5\u2010triazapentadienate\u2010Pd<jats:sup>II<\/jats:sup> complexes [Pd{HN=C(OR)NC(OR)=NH}<jats:sub>2<\/jats:sub>] (<jats:bold>6<\/jats:bold>) [R = Me (<jats:bold>6a<\/jats:bold>), Et (<jats:bold>6b<\/jats:bold>), <jats:italic>n<\/jats:italic>Pr (<jats:bold>6c<\/jats:bold>), (CH<jats:sub>2<\/jats:sub>)<jats:sub>2<\/jats:sub>OMe (<jats:bold>6d<\/jats:bold>)], respectively, are formed and isolated as a mixture of isomers in good yields. All these compounds have been characterized by IR, <jats:sup>1<\/jats:sup>H and <jats:sup>13<\/jats:sup>C NMR spectroscopy, ESI\u2010MS, elemental analyses and, in the case of <jats:bold>2c<\/jats:bold>, by XRD.<\/jats:p>","DOI":"10.1002\/ejic.201000898","type":"journal-article","created":{"date-parts":[[2010,12,9]],"date-time":"2010-12-09T05:26:35Z","timestamp":1291872395000},"page":"377-383","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Pd<sup>II<\/sup>\u2010Promoted Single\u2010Pot Template Transformations of Benzonitriles, Cyanoguanidine and Sodium Dicyanamide with the Formation of Symmetrical and Asymmetrical (1,3,5\u2010Triazapentadienate)palladium(II) Complexes"],"prefix":"10.1002","volume":"2011","author":[{"given":"Maximilian N.","family":"Kopylovich","sequence":"first","affiliation":[]},{"given":"Jamal","family":"Lasri","sequence":"additional","affiliation":[]},{"given":"M. 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