Oxidative Addition of Tetrachloro-1,2-benzoquinone to lambda(3)-Cyclotriphosphazanes. An Unusual Ring Contraction-Rearrangement
The lambda(3)-cyclotriphosphazanes, [EtNP(OR)](3) [R = 2,6-Me(2)C(6)H(3) (1), 4-BrC(6)H(4) (2), or CH(2)CF(3)(3)], on treatment with tetrachloro-1,2-benzoquinone (TCB) give the lambda(5)-cyclodiphosphazanes, [EtNP(O(2)C(6)Cl(4))(OR)][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (5-7) by an unusual ring contr...
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Veröffentlicht in: | Inorganic chemistry 1999-03, Vol.38 (6), p.1093-1098 |
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description | The lambda(3)-cyclotriphosphazanes, [EtNP(OR)](3) [R = 2,6-Me(2)C(6)H(3) (1), 4-BrC(6)H(4) (2), or CH(2)CF(3)(3)], on treatment with tetrachloro-1,2-benzoquinone (TCB) give the lambda(5)-cyclodiphosphazanes, [EtNP(O(2)C(6)Cl(4))(OR)][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (5-7) by an unusual ring contraction-rearrangement. The reaction of the mixed substituent lambda(3)-cyclotriphosphazane, [(EtN)(3)P(3)(OR)(2)(OR')] [R = 2,6-Me(2)C(6)H(3), R' = 4-BrC(6)H(4)] (4), with TCB gives the lambda(5)-cyclodiphosphazane, [EtNP(O(2)C(6)Cl(4))(OR')][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (8), in which 4-bromophenoxide resides on one of the ring phosphorus atoms. The lambda(3)-bicyclic tetraphosphapentazane, (EtN)(5)P(4)(OPh)(2), on treatment with TCB undergoes a double ring contraction-rearrangement to give the lambda(5)-cyclodiphosphazane, (EtN)[(EtN)(2)P(2)(O(2)C(6)Cl(4))(2)(OPh)](2) (9). Variable-temperature and high-field (31)P NMR studies indicate the presence of more than one isomer in solution for the rearranged products 5-9. The solid state structure of 8 reveals a trans arrangement of the substituents with respect to the P(2)N(2) ring in contrast to the gauche arrangement observed for 5. |
doi_str_mv | 10.1021/ic980459i |
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An Unusual Ring Contraction-Rearrangement</title><source>ACS Publications</source><creator>Thirupathi, Natesan ; Krishnamurthy, Setharampattu S. ; Nethaji, Munirathinam</creator><creatorcontrib>Thirupathi, Natesan ; Krishnamurthy, Setharampattu S. ; Nethaji, Munirathinam</creatorcontrib><description>The lambda(3)-cyclotriphosphazanes, [EtNP(OR)](3) [R = 2,6-Me(2)C(6)H(3) (1), 4-BrC(6)H(4) (2), or CH(2)CF(3)(3)], on treatment with tetrachloro-1,2-benzoquinone (TCB) give the lambda(5)-cyclodiphosphazanes, [EtNP(O(2)C(6)Cl(4))(OR)][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (5-7) by an unusual ring contraction-rearrangement. The reaction of the mixed substituent lambda(3)-cyclotriphosphazane, [(EtN)(3)P(3)(OR)(2)(OR')] [R = 2,6-Me(2)C(6)H(3), R' = 4-BrC(6)H(4)] (4), with TCB gives the lambda(5)-cyclodiphosphazane, [EtNP(O(2)C(6)Cl(4))(OR')][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (8), in which 4-bromophenoxide resides on one of the ring phosphorus atoms. The lambda(3)-bicyclic tetraphosphapentazane, (EtN)(5)P(4)(OPh)(2), on treatment with TCB undergoes a double ring contraction-rearrangement to give the lambda(5)-cyclodiphosphazane, (EtN)[(EtN)(2)P(2)(O(2)C(6)Cl(4))(2)(OPh)](2) (9). Variable-temperature and high-field (31)P NMR studies indicate the presence of more than one isomer in solution for the rearranged products 5-9. The solid state structure of 8 reveals a trans arrangement of the substituents with respect to the P(2)N(2) ring in contrast to the gauche arrangement observed for 5.</description><identifier>EISSN: 1520-510X</identifier><identifier>DOI: 10.1021/ic980459i</identifier><identifier>PMID: 11670889</identifier><language>eng</language><publisher>United States</publisher><ispartof>Inorganic chemistry, 1999-03, Vol.38 (6), p.1093-1098</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11670889$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Thirupathi, Natesan</creatorcontrib><creatorcontrib>Krishnamurthy, Setharampattu S.</creatorcontrib><creatorcontrib>Nethaji, Munirathinam</creatorcontrib><title>Oxidative Addition of Tetrachloro-1,2-benzoquinone to lambda(3)-Cyclotriphosphazanes. An Unusual Ring Contraction-Rearrangement</title><title>Inorganic chemistry</title><addtitle>Inorg Chem</addtitle><description>The lambda(3)-cyclotriphosphazanes, [EtNP(OR)](3) [R = 2,6-Me(2)C(6)H(3) (1), 4-BrC(6)H(4) (2), or CH(2)CF(3)(3)], on treatment with tetrachloro-1,2-benzoquinone (TCB) give the lambda(5)-cyclodiphosphazanes, [EtNP(O(2)C(6)Cl(4))(OR)][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (5-7) by an unusual ring contraction-rearrangement. The reaction of the mixed substituent lambda(3)-cyclotriphosphazane, [(EtN)(3)P(3)(OR)(2)(OR')] [R = 2,6-Me(2)C(6)H(3), R' = 4-BrC(6)H(4)] (4), with TCB gives the lambda(5)-cyclodiphosphazane, [EtNP(O(2)C(6)Cl(4))(OR')][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (8), in which 4-bromophenoxide resides on one of the ring phosphorus atoms. The lambda(3)-bicyclic tetraphosphapentazane, (EtN)(5)P(4)(OPh)(2), on treatment with TCB undergoes a double ring contraction-rearrangement to give the lambda(5)-cyclodiphosphazane, (EtN)[(EtN)(2)P(2)(O(2)C(6)Cl(4))(2)(OPh)](2) (9). Variable-temperature and high-field (31)P NMR studies indicate the presence of more than one isomer in solution for the rearranged products 5-9. The solid state structure of 8 reveals a trans arrangement of the substituents with respect to the P(2)N(2) ring in contrast to the gauche arrangement observed for 5.</description><issn>1520-510X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><recordid>eNo1kE1LwzAAhoMgbk4P_gHJcYKZ-Wiz5jiKXyAMxgbeStokW6RNapOK28W_bofz9F4eHt73BeCG4BnBlDzYSmQ4SYU9A2OSUoxSgt9H4DKED4yxYAm_ACNC-BxnmRiDn-W3VTLaLw0XStlovYPewLWOnax2te88IvcUldod_GdvnXcaRg9r2ZRKTtkdyvdV7WNn250P7U4epNNhBhcOblwfelnDlXVbmHt3FB71aKVl10m31Y128QqcG1kHfX3KCdg8Pa7zF_S2fH7NF2-opVhExBOClTGM0kpRY7IEU8MTpUymqOQCJ_NSlISmldKKK4OxZpInA5xVMuVlyiZg-udtu2GHDrFobKh0XQ99fR8KkqWCcTacMqC3J7QvG62KtrON7PbF_2nsF-CVbhU</recordid><startdate>19990322</startdate><enddate>19990322</enddate><creator>Thirupathi, Natesan</creator><creator>Krishnamurthy, Setharampattu S.</creator><creator>Nethaji, Munirathinam</creator><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>19990322</creationdate><title>Oxidative Addition of Tetrachloro-1,2-benzoquinone to lambda(3)-Cyclotriphosphazanes. An Unusual Ring Contraction-Rearrangement</title><author>Thirupathi, Natesan ; Krishnamurthy, Setharampattu S. ; Nethaji, Munirathinam</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p209t-6410dff322cd2ff8402f64ddf8d2a69047b9b125cded6df00e3a642cd8ca56b53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thirupathi, Natesan</creatorcontrib><creatorcontrib>Krishnamurthy, Setharampattu S.</creatorcontrib><creatorcontrib>Nethaji, Munirathinam</creatorcontrib><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thirupathi, Natesan</au><au>Krishnamurthy, Setharampattu S.</au><au>Nethaji, Munirathinam</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative Addition of Tetrachloro-1,2-benzoquinone to lambda(3)-Cyclotriphosphazanes. An Unusual Ring Contraction-Rearrangement</atitle><jtitle>Inorganic chemistry</jtitle><addtitle>Inorg Chem</addtitle><date>1999-03-22</date><risdate>1999</risdate><volume>38</volume><issue>6</issue><spage>1093</spage><epage>1098</epage><pages>1093-1098</pages><eissn>1520-510X</eissn><abstract>The lambda(3)-cyclotriphosphazanes, [EtNP(OR)](3) [R = 2,6-Me(2)C(6)H(3) (1), 4-BrC(6)H(4) (2), or CH(2)CF(3)(3)], on treatment with tetrachloro-1,2-benzoquinone (TCB) give the lambda(5)-cyclodiphosphazanes, [EtNP(O(2)C(6)Cl(4))(OR)][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (5-7) by an unusual ring contraction-rearrangement. The reaction of the mixed substituent lambda(3)-cyclotriphosphazane, [(EtN)(3)P(3)(OR)(2)(OR')] [R = 2,6-Me(2)C(6)H(3), R' = 4-BrC(6)H(4)] (4), with TCB gives the lambda(5)-cyclodiphosphazane, [EtNP(O(2)C(6)Cl(4))(OR')][EtNP(O(2)C(6)Cl(4)){N(Et)P(OR)(2)}] (8), in which 4-bromophenoxide resides on one of the ring phosphorus atoms. The lambda(3)-bicyclic tetraphosphapentazane, (EtN)(5)P(4)(OPh)(2), on treatment with TCB undergoes a double ring contraction-rearrangement to give the lambda(5)-cyclodiphosphazane, (EtN)[(EtN)(2)P(2)(O(2)C(6)Cl(4))(2)(OPh)](2) (9). Variable-temperature and high-field (31)P NMR studies indicate the presence of more than one isomer in solution for the rearranged products 5-9. The solid state structure of 8 reveals a trans arrangement of the substituents with respect to the P(2)N(2) ring in contrast to the gauche arrangement observed for 5.</abstract><cop>United States</cop><pmid>11670889</pmid><doi>10.1021/ic980459i</doi><tpages>6</tpages></addata></record> |
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title | Oxidative Addition of Tetrachloro-1,2-benzoquinone to lambda(3)-Cyclotriphosphazanes. An Unusual Ring Contraction-Rearrangement |
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