Tetrazolyl and tetrazolylidene complexes of gold: A synthetic and structural study

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dc.contributor.authorGabrielli W.F.
dc.contributor.authorNogai S.D.
dc.contributor.authorMcKenzie J.M.
dc.contributor.authorCronje S.
dc.contributor.authorRaubenheimer H.G.
dc.contributor.authorGabrielli W.F.
dc.contributor.authorNogai S.D.
dc.contributor.authorMcKenzie J.M.
dc.contributor.authorCronje S.
dc.contributor.authorRaubenheimer H.G.
dc.date.accessioned2011-05-15T16:05:14Z
dc.date.accessioned2011-05-15T16:05:14Z
dc.date.available2011-05-15T16:05:14Z
dc.date.available2011-05-15T16:05:14Z
dc.date.issued2009
dc.date.issued2009
dc.description.abstractLithiation of 1-benzyl-1H-tetrazole followed by transmetallation with [AuCl(PPh3)], [Au(C6F5)(tht)] or [AuCl(tht)] (tht = tetrahydrothiophene) and subsequent alkylation afforded cationic 1-benzyl-4-methyl-4,5-dihydro-1H-1,2,3,4-tetrazol-5-ylidene(triphenylphosphine) gold(i), 1, neutral 1-benzyl-4-methyl-4,5-dihydro-1H-1,2,3,4-tetrazol-5- ylidene(pentafluorophenyl)gold(i), 2, and a cationic biscarbene complex, bis(1-benzyl-4-methyl-4,5-dihydro-1H-1,2,3,4-tetrazol-5-ylidene)gold(i), 3. The first complex underwent a homoleptic rearrangement in solution to form 3. Reaction of [Au(N3)PPh3] with the three isocyanides (CH3)2C6H3NC, tBuNC and CyNC, respectively, yielded the corresponding neutral tetrazolyl(phosphine) complexes of gold, [1-(2,6-dimethylphenyl)-1H-tetrazol-5-yl](triphenylphosphine) gold(i), 4, [1-(tert-butyl)-1H-tetrazol-5-yl](triphenylphosphine)gold(i), 6, and [1-(cyclohexyl)-1H-tetrazol-5-yl](triphenylphosphine)gold(i), 7. Alkylation of 4 with methyl triflate on N4 allowed isolation of the crystalline carbene complex 1-(2,6-dimethylphenyl)-4-methyl-4,5-dihydro-1H-1,2,3,4-tetrazol- 5-ylidene)(triphenylphosphine)gold(i), 5. Complex 7 was not isolable in pure form but converts by isocyanide substitution of triphenylphosphine into [1-cyclohexylisocyanide][1-(cyclohexyl)-1H-tetrazol-5-yl]gold(i), 8. From a product mixture of 7 and 8 the transformed molecules [(cyclohexylamino)(ethoxy) carbene](1-cyclohexyl-1H-tetrazol-5-yl)gold(i), 9, and [bis(cyclohexylamino) carbene](1-cyclohexyltetrazol-5-yl)gold(i), 10, co-crystallised spontaneously after a long time at -20 °C. © 2009 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
dc.description.abstractLithiation of 1-benzyl-1H-tetrazole followed by transmetallation with [AuCl(PPh3)], [Au(C6F5)(tht)] or [AuCl(tht)] (tht = tetrahydrothiophene) and subsequent alkylation afforded cationic 1-benzyl-4-methyl-4,5-dihydro-1H-1,2,3,4-tetrazol-5-ylidene(triphenylphosphine) gold(i), 1, neutral 1-benzyl-4-methyl-4,5-dihydro-1H-1,2,3,4-tetrazol-5- ylidene(pentafluorophenyl)gold(i), 2, and a cationic biscarbene complex, bis(1-benzyl-4-methyl-4,5-dihydro-1H-1,2,3,4-tetrazol-5-ylidene)gold(i), 3. The first complex underwent a homoleptic rearrangement in solution to form 3. Reaction of [Au(N3)PPh3] with the three isocyanides (CH3)2C6H3NC, tBuNC and CyNC, respectively, yielded the corresponding neutral tetrazolyl(phosphine) complexes of gold, [1-(2,6-dimethylphenyl)-1H-tetrazol-5-yl](triphenylphosphine) gold(i), 4, [1-(tert-butyl)-1H-tetrazol-5-yl](triphenylphosphine)gold(i), 6, and [1-(cyclohexyl)-1H-tetrazol-5-yl](triphenylphosphine)gold(i), 7. Alkylation of 4 with methyl triflate on N4 allowed isolation of the crystalline carbene complex 1-(2,6-dimethylphenyl)-4-methyl-4,5-dihydro-1H-1,2,3,4-tetrazol- 5-ylidene)(triphenylphosphine)gold(i), 5. Complex 7 was not isolable in pure form but converts by isocyanide substitution of triphenylphosphine into [1-cyclohexylisocyanide][1-(cyclohexyl)-1H-tetrazol-5-yl]gold(i), 8. From a product mixture of 7 and 8 the transformed molecules [(cyclohexylamino)(ethoxy) carbene](1-cyclohexyl-1H-tetrazol-5-yl)gold(i), 9, and [bis(cyclohexylamino) carbene](1-cyclohexyltetrazol-5-yl)gold(i), 10, co-crystallised spontaneously after a long time at -20 °C. © 2009 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
dc.description.versionArticle
dc.description.versionArticle
dc.identifier.citationNew Journal of Chemistry
dc.identifier.citation33
dc.identifier.citation11
dc.identifier.citationNew Journal of Chemistry
dc.identifier.citation33
dc.identifier.citation11
dc.identifier.issn11440546
dc.identifier.issn11440546
dc.identifier.other10.1039/b907022b
dc.identifier.other10.1039/b907022b
dc.identifier.urihttp://hdl.handle.net/10019.1/13037
dc.identifier.urihttp://hdl.handle.net/10019.1/13037
dc.subjectcarbenoid; cyanide; gold complex; phosphine derivative; trifluoromethanesulfonic acid; unclassified drug; alkylation; article; chemical reaction kinetics; chemical structure; complex formation; crystallography; lithiation; nuclear magnetic resonance spectroscopy; priority journal
dc.subjectcarbenoid
dc.subjectcyanide
dc.subjectgold complex
dc.subjectphosphine derivative
dc.subjecttrifluoromethanesulfonic acid
dc.subjectunclassified drug
dc.subjectalkylation
dc.subjectarticle
dc.subjectchemical reaction kinetics
dc.subjectchemical structure
dc.subjectcomplex formation
dc.subjectcrystallography
dc.subjectlithiation
dc.subjectnuclear magnetic resonance spectroscopy
dc.subjectpriority journal
dc.titleTetrazolyl and tetrazolylidene complexes of gold: A synthetic and structural study
dc.titleTetrazolyl and tetrazolylidene complexes of gold: A synthetic and structural study
dc.typeArticle
dc.typeArticle
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