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Article: Synthesis, crystal structure of ruthenium 1,2-naphthoquinone-1-oxime complex and its mediated C-C coupling reactions of terminal alkynes

TitleSynthesis, crystal structure of ruthenium 1,2-naphthoquinone-1-oxime complex and its mediated C-C coupling reactions of terminal alkynes
Authors
Keywords1,2-naphthoquinone-1-oxime
Crystal structure
Ruthenium
Issue Date2003
PublisherZhongguo Kexueyuan, Shanghai Youji Huaxue Yanjiusuo. The Journal's web site is located at http://www.sioc-journal.cn/zghx/index_en.asp
Citation
Chinese Journal Of Chemistry, 2003, v. 21 n. 10, p. 1315-1319 How to Cite?
AbstractSubstituted decarbonylation reaction of ruthenium 1,2-naphthoquinone-1- oxime (1-nqo) complex, cis-, cis-[Ru{η 2-N(O)C 10-H 6O} 2(CO) 2] (1), with acetonitrile gave cis-, cis-[Ru{η 2-N(O)C 10H 6O} 2(CO) (NCMe)] (2). Complex 2 was fully characterized by 1H NMR, FAB MS, IR spectra and single crystal X-ray analysis. Complex 2 maintains the coordination structure of 1 with the two naphthoquinonic oxygen atoms, as well as the two oximato nitrogen atoms located cis to each other, showing that there is no ligand rearrangement of the 1-nqo ligands during the substitution reaction. The carbonyl group originally trans to the naphthoquinonic oxygen in one 1-nqo ligand is left in its original position [O(5)-Ru-C(1), 174.0(6)°], while the other one originally trans to the oximato group of the other 1-nqo ligand is substituted by NCMe [N(1)-Ru-N(3), 170.6(6)°]. This shows that the carbonyl trans to oximato group is more labile than the one trans to naphthoquinonic O atom towards substitution. This is probably due to the comparatively stronger π back bonding from ruthenium metal to the carbonyl group trans to naphthoquinonic O atom, than the one trans to oximato group, resulting in the comparatively weaker Ru-CO bond for the latter and consequently easier replacement of this carbonyl. Selected coupling of phenylacetylene mediated by 2 gave a single trans-dimerization product 3, while 2 mediated coupling reaction of methyl propiolate produced three products: one trans-dimerization product 4 and two cyclotrimeric products 5 and 6.
Persistent Identifierhttp://hdl.handle.net/10722/69136
ISSN
2015 Impact Factor: 1.872
2015 SCImago Journal Rankings: 0.441
References

 

DC FieldValueLanguage
dc.contributor.authorSun, Ken_HK
dc.contributor.authorWong, WTen_HK
dc.contributor.authorLiu, XXen_HK
dc.contributor.authorZhang, BYen_HK
dc.date.accessioned2010-09-06T06:10:54Z-
dc.date.available2010-09-06T06:10:54Z-
dc.date.issued2003en_HK
dc.identifier.citationChinese Journal Of Chemistry, 2003, v. 21 n. 10, p. 1315-1319en_HK
dc.identifier.issn1001-604Xen_HK
dc.identifier.urihttp://hdl.handle.net/10722/69136-
dc.description.abstractSubstituted decarbonylation reaction of ruthenium 1,2-naphthoquinone-1- oxime (1-nqo) complex, cis-, cis-[Ru{η 2-N(O)C 10-H 6O} 2(CO) 2] (1), with acetonitrile gave cis-, cis-[Ru{η 2-N(O)C 10H 6O} 2(CO) (NCMe)] (2). Complex 2 was fully characterized by 1H NMR, FAB MS, IR spectra and single crystal X-ray analysis. Complex 2 maintains the coordination structure of 1 with the two naphthoquinonic oxygen atoms, as well as the two oximato nitrogen atoms located cis to each other, showing that there is no ligand rearrangement of the 1-nqo ligands during the substitution reaction. The carbonyl group originally trans to the naphthoquinonic oxygen in one 1-nqo ligand is left in its original position [O(5)-Ru-C(1), 174.0(6)°], while the other one originally trans to the oximato group of the other 1-nqo ligand is substituted by NCMe [N(1)-Ru-N(3), 170.6(6)°]. This shows that the carbonyl trans to oximato group is more labile than the one trans to naphthoquinonic O atom towards substitution. This is probably due to the comparatively stronger π back bonding from ruthenium metal to the carbonyl group trans to naphthoquinonic O atom, than the one trans to oximato group, resulting in the comparatively weaker Ru-CO bond for the latter and consequently easier replacement of this carbonyl. Selected coupling of phenylacetylene mediated by 2 gave a single trans-dimerization product 3, while 2 mediated coupling reaction of methyl propiolate produced three products: one trans-dimerization product 4 and two cyclotrimeric products 5 and 6.en_HK
dc.languageengen_HK
dc.publisherZhongguo Kexueyuan, Shanghai Youji Huaxue Yanjiusuo. The Journal's web site is located at http://www.sioc-journal.cn/zghx/index_en.aspen_HK
dc.relation.ispartofChinese Journal of Chemistryen_HK
dc.subject1,2-naphthoquinone-1-oximeen_HK
dc.subjectCrystal structureen_HK
dc.subjectRutheniumen_HK
dc.titleSynthesis, crystal structure of ruthenium 1,2-naphthoquinone-1-oxime complex and its mediated C-C coupling reactions of terminal alkynesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1001-604X&volume=21&spage=1315&epage=1319&date=2003&atitle=Synthesis,+crystal+structure+of+ruthenium+1,2-naphthoquinone-1-oxime+complex+and+its+mediated+C_C+coupling+reactions+of+terminal+alkynesen_HK
dc.identifier.emailWong, WT: wtwong@hku.hken_HK
dc.identifier.authorityWong, WT=rp00811en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/cjoc.20030211016-
dc.identifier.scopuseid_2-s2.0-19444363207en_HK
dc.identifier.hkuros91942en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-19444363207&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume21en_HK
dc.identifier.issue10en_HK
dc.identifier.spage1315en_HK
dc.identifier.epage1319en_HK
dc.publisher.placeChinaen_HK
dc.identifier.scopusauthoridSun, K=55436314000en_HK
dc.identifier.scopusauthoridWong, WT=7403973084en_HK
dc.identifier.scopusauthoridLiu, XX=22958433500en_HK
dc.identifier.scopusauthoridZhang, BY=7406906380en_HK

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