Palladium(II) Aryloxides of Pd(2,6-(CH 2 NMe 2 ) 2 C 6 H 3 )(OC 6 H 4 -X-p) (X = Me, NO 2 ): Synthesis, Property and Reactivity towards Diphenyliodium Chloride
para-Substituted phenoxide derivatives of Pd(II) having an NCN pincer, Pd(NCN)($OC_6H_4$-p-X) (NCN = 2,6-$(CH_2NMe_2)_2C_6H_3$; X = $NO_2$ (1), Me (2)) were prepared by the reaction of Pd(NCN)($OSO_2CF_3$) with equi-molar amount of $NaOC_6H_4$-p-X. Treatment of Pd(NCN)($OSO_2CF_3$) with an excess am...
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Veröffentlicht in: | Bulletin of the Korean Chemical Society 2011, Vol.32 (8), p.2711-2716 |
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creator | Jung, Hyun-Sang Park, Yun-Sik Seul, Jung-Min Kim, Jong-Sook Lee, Ho-Jin Park, Soon-Heum |
description | para-Substituted phenoxide derivatives of Pd(II) having an NCN pincer, Pd(NCN)($OC_6H_4$-p-X) (NCN = 2,6-$(CH_2NMe_2)_2C_6H_3$; X = $NO_2$ (1), Me (2)) were prepared by the reaction of Pd(NCN)($OSO_2CF_3$) with equi-molar amount of $NaOC_6H_4$-p-X. Treatment of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4$-p-Me affords the hydrogen-bonding adduct complex 3 ($2{\cdot}HOC_6H_4$-p-Me). Complex 3 can also be obtained from benzene solution of 2 in the presence of free $HOC_6H_4$-p-Me. Complex 1 does not undergo adduct formation with $HOC_6H_4-p-NO_2$ neither from metathesis reaction of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4-p-NO_2$ nor from treatment of 1 with free $HOC_6H_4-p-NO_2$. Complex 3 undergoes fast exchange of the coordinated p-cresolate with the hydrogen-bonding p-cresol. Complex 2 undergoes ${\sigma}$-ligand exchange reaction with $HOC_6H_4-p-NO_2$ to give 1. The exchange reaction, however, is irreversible as readily anticipated from their respective $pK_a$ values of the phenol derivatives. Reaction of 2 with diphenyliodium chloride quantitatively produced Pd(NCN)Cl and PhI along with liberation of O-phenylated product $PhOC_6H_4$-p-Me which was identified by GC/MS spectroscopy. |
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fullrecord | <record><control><sourceid>kisti</sourceid><recordid>TN_cdi_kisti_ndsl_JAKO201129460143894</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>JAKO201129460143894</sourcerecordid><originalsourceid>FETCH-kisti_ndsl_JAKO2011294601438943</originalsourceid><addsrcrecordid>eNqNjt1KwzAYhoMoWHT38J0ILTTQJmlnBA9GdXTK1qIe7GxEk9FgbEoSf3o13qodegEevH_wHLxHKMoJ4bjgjB-jKCMFxYSX7BTNvNfPWUHpvJxTHqHvVhgjpH5_i1erBBZuNPZLS-XB7qGVMUlLHFc1ENis1eTJpApKqIFCEje_lQHe4iGBeAvXsFYpbJoDegWPYx865bVPoXV2UC6MIHoJD0q8BP2hpxnsp3DSw40eOtWPRtvDGag6Y9304xyd7IXxavaXZ-hieftU1fhV-6B3vfRmd7e4b0iW54SzMssZveSM_pf7AcSnUjY</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Palladium(II) Aryloxides of Pd(2,6-(CH 2 NMe 2 ) 2 C 6 H 3 )(OC 6 H 4 -X-p) (X = Me, NO 2 ): Synthesis, Property and Reactivity towards Diphenyliodium Chloride</title><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Jung, Hyun-Sang ; Park, Yun-Sik ; Seul, Jung-Min ; Kim, Jong-Sook ; Lee, Ho-Jin ; Park, Soon-Heum</creator><creatorcontrib>Jung, Hyun-Sang ; Park, Yun-Sik ; Seul, Jung-Min ; Kim, Jong-Sook ; Lee, Ho-Jin ; Park, Soon-Heum</creatorcontrib><description>para-Substituted phenoxide derivatives of Pd(II) having an NCN pincer, Pd(NCN)($OC_6H_4$-p-X) (NCN = 2,6-$(CH_2NMe_2)_2C_6H_3$; X = $NO_2$ (1), Me (2)) were prepared by the reaction of Pd(NCN)($OSO_2CF_3$) with equi-molar amount of $NaOC_6H_4$-p-X. Treatment of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4$-p-Me affords the hydrogen-bonding adduct complex 3 ($2{\cdot}HOC_6H_4$-p-Me). Complex 3 can also be obtained from benzene solution of 2 in the presence of free $HOC_6H_4$-p-Me. Complex 1 does not undergo adduct formation with $HOC_6H_4-p-NO_2$ neither from metathesis reaction of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4-p-NO_2$ nor from treatment of 1 with free $HOC_6H_4-p-NO_2$. Complex 3 undergoes fast exchange of the coordinated p-cresolate with the hydrogen-bonding p-cresol. Complex 2 undergoes ${\sigma}$-ligand exchange reaction with $HOC_6H_4-p-NO_2$ to give 1. The exchange reaction, however, is irreversible as readily anticipated from their respective $pK_a$ values of the phenol derivatives. Reaction of 2 with diphenyliodium chloride quantitatively produced Pd(NCN)Cl and PhI along with liberation of O-phenylated product $PhOC_6H_4$-p-Me which was identified by GC/MS spectroscopy.</description><identifier>ISSN: 0253-2964</identifier><identifier>EISSN: 1229-5949</identifier><language>kor</language><ispartof>Bulletin of the Korean Chemical Society, 2011, Vol.32 (8), p.2711-2716</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,778,782,883,4012</link.rule.ids></links><search><creatorcontrib>Jung, Hyun-Sang</creatorcontrib><creatorcontrib>Park, Yun-Sik</creatorcontrib><creatorcontrib>Seul, Jung-Min</creatorcontrib><creatorcontrib>Kim, Jong-Sook</creatorcontrib><creatorcontrib>Lee, Ho-Jin</creatorcontrib><creatorcontrib>Park, Soon-Heum</creatorcontrib><title>Palladium(II) Aryloxides of Pd(2,6-(CH 2 NMe 2 ) 2 C 6 H 3 )(OC 6 H 4 -X-p) (X = Me, NO 2 ): Synthesis, Property and Reactivity towards Diphenyliodium Chloride</title><title>Bulletin of the Korean Chemical Society</title><addtitle>Bulletin of the Korean chemical society</addtitle><description>para-Substituted phenoxide derivatives of Pd(II) having an NCN pincer, Pd(NCN)($OC_6H_4$-p-X) (NCN = 2,6-$(CH_2NMe_2)_2C_6H_3$; X = $NO_2$ (1), Me (2)) were prepared by the reaction of Pd(NCN)($OSO_2CF_3$) with equi-molar amount of $NaOC_6H_4$-p-X. Treatment of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4$-p-Me affords the hydrogen-bonding adduct complex 3 ($2{\cdot}HOC_6H_4$-p-Me). Complex 3 can also be obtained from benzene solution of 2 in the presence of free $HOC_6H_4$-p-Me. Complex 1 does not undergo adduct formation with $HOC_6H_4-p-NO_2$ neither from metathesis reaction of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4-p-NO_2$ nor from treatment of 1 with free $HOC_6H_4-p-NO_2$. Complex 3 undergoes fast exchange of the coordinated p-cresolate with the hydrogen-bonding p-cresol. Complex 2 undergoes ${\sigma}$-ligand exchange reaction with $HOC_6H_4-p-NO_2$ to give 1. The exchange reaction, however, is irreversible as readily anticipated from their respective $pK_a$ values of the phenol derivatives. Reaction of 2 with diphenyliodium chloride quantitatively produced Pd(NCN)Cl and PhI along with liberation of O-phenylated product $PhOC_6H_4$-p-Me which was identified by GC/MS spectroscopy.</description><issn>0253-2964</issn><issn>1229-5949</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>JDI</sourceid><recordid>eNqNjt1KwzAYhoMoWHT38J0ILTTQJmlnBA9GdXTK1qIe7GxEk9FgbEoSf3o13qodegEevH_wHLxHKMoJ4bjgjB-jKCMFxYSX7BTNvNfPWUHpvJxTHqHvVhgjpH5_i1erBBZuNPZLS-XB7qGVMUlLHFc1ENis1eTJpApKqIFCEje_lQHe4iGBeAvXsFYpbJoDegWPYx865bVPoXV2UC6MIHoJD0q8BP2hpxnsp3DSw40eOtWPRtvDGag6Y9304xyd7IXxavaXZ-hieftU1fhV-6B3vfRmd7e4b0iW54SzMssZveSM_pf7AcSnUjY</recordid><startdate>2011</startdate><enddate>2011</enddate><creator>Jung, Hyun-Sang</creator><creator>Park, Yun-Sik</creator><creator>Seul, Jung-Min</creator><creator>Kim, Jong-Sook</creator><creator>Lee, Ho-Jin</creator><creator>Park, Soon-Heum</creator><scope>JDI</scope></search><sort><creationdate>2011</creationdate><title>Palladium(II) Aryloxides of Pd(2,6-(CH 2 NMe 2 ) 2 C 6 H 3 )(OC 6 H 4 -X-p) (X = Me, NO 2 ): Synthesis, Property and Reactivity towards Diphenyliodium Chloride</title><author>Jung, Hyun-Sang ; Park, Yun-Sik ; Seul, Jung-Min ; Kim, Jong-Sook ; Lee, Ho-Jin ; Park, Soon-Heum</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-kisti_ndsl_JAKO2011294601438943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>kor</language><creationdate>2011</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jung, Hyun-Sang</creatorcontrib><creatorcontrib>Park, Yun-Sik</creatorcontrib><creatorcontrib>Seul, Jung-Min</creatorcontrib><creatorcontrib>Kim, Jong-Sook</creatorcontrib><creatorcontrib>Lee, Ho-Jin</creatorcontrib><creatorcontrib>Park, Soon-Heum</creatorcontrib><collection>KoreaScience</collection><jtitle>Bulletin of the Korean Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jung, Hyun-Sang</au><au>Park, Yun-Sik</au><au>Seul, Jung-Min</au><au>Kim, Jong-Sook</au><au>Lee, Ho-Jin</au><au>Park, Soon-Heum</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium(II) Aryloxides of Pd(2,6-(CH 2 NMe 2 ) 2 C 6 H 3 )(OC 6 H 4 -X-p) (X = Me, NO 2 ): Synthesis, Property and Reactivity towards Diphenyliodium Chloride</atitle><jtitle>Bulletin of the Korean Chemical Society</jtitle><addtitle>Bulletin of the Korean chemical society</addtitle><date>2011</date><risdate>2011</risdate><volume>32</volume><issue>8</issue><spage>2711</spage><epage>2716</epage><pages>2711-2716</pages><issn>0253-2964</issn><eissn>1229-5949</eissn><abstract>para-Substituted phenoxide derivatives of Pd(II) having an NCN pincer, Pd(NCN)($OC_6H_4$-p-X) (NCN = 2,6-$(CH_2NMe_2)_2C_6H_3$; X = $NO_2$ (1), Me (2)) were prepared by the reaction of Pd(NCN)($OSO_2CF_3$) with equi-molar amount of $NaOC_6H_4$-p-X. Treatment of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4$-p-Me affords the hydrogen-bonding adduct complex 3 ($2{\cdot}HOC_6H_4$-p-Me). Complex 3 can also be obtained from benzene solution of 2 in the presence of free $HOC_6H_4$-p-Me. Complex 1 does not undergo adduct formation with $HOC_6H_4-p-NO_2$ neither from metathesis reaction of Pd(NCN)($OSO_2CF_3$) with an excess amount of $NaOC_6H_4-p-NO_2$ nor from treatment of 1 with free $HOC_6H_4-p-NO_2$. Complex 3 undergoes fast exchange of the coordinated p-cresolate with the hydrogen-bonding p-cresol. Complex 2 undergoes ${\sigma}$-ligand exchange reaction with $HOC_6H_4-p-NO_2$ to give 1. The exchange reaction, however, is irreversible as readily anticipated from their respective $pK_a$ values of the phenol derivatives. Reaction of 2 with diphenyliodium chloride quantitatively produced Pd(NCN)Cl and PhI along with liberation of O-phenylated product $PhOC_6H_4$-p-Me which was identified by GC/MS spectroscopy.</abstract><oa>free_for_read</oa></addata></record> |
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title | Palladium(II) Aryloxides of Pd(2,6-(CH 2 NMe 2 ) 2 C 6 H 3 )(OC 6 H 4 -X-p) (X = Me, NO 2 ): Synthesis, Property and Reactivity towards Diphenyliodium Chloride |
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