Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene
Starting from the same ethylenediamine species, three valuable carbene precursors were synthesized under differing conditions: a tridentate dianionic N-heterocyclic carbene bearing an aniline, a phenol and a central dihydroimidazolium salt, its benzimidazolium isomer by intramolecular rearrangement...
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| Veröffentlicht in: | Chemical science (Cambridge) 2013-01, Vol.4 (5), p.2117-2121 |
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| container_title | Chemical science (Cambridge) |
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| creator | Despagnet-Ayoub, Emmanuelle Miqueu, Karinne Sotiropoulos, Jean-Marc Henling, Lawrence M Day, Michael W Labinger, Jay A Bercaw, John E |
| description | Starting from the same ethylenediamine species, three valuable carbene precursors were synthesized under differing conditions: a tridentate dianionic N-heterocyclic carbene bearing an aniline, a phenol and a central dihydroimidazolium salt, its benzimidazolium isomer by intramolecular rearrangement and a dicationic benzimidazolium-benzoxazolium salt by changing the Broensted acid from HCl to HBF sub(4). A DFT study was performed to understand the rearrangement pathway. The structure of a bis[(NCO)carbene] zirconium complex was determined. |
| doi_str_mv | 10.1039/c3sc22171g |
| format | Article |
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A DFT study was performed to understand the rearrangement pathway. The structure of a bis[(NCO)carbene] zirconium complex was determined.</description><subject>Bearing</subject><subject>Carbenes</subject><subject>Chemical Sciences</subject><subject>Coordination chemistry</subject><subject>Isomers</subject><subject>Pathways</subject><subject>Phenol</subject><subject>Precursors</subject><subject>Synthesis</subject><subject>Zirconium</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkU1Lw0AQhoMoWLQXf8EeVYjuRz52j6WoFYpe7DlMJ5N2S7Kpu6mYf29CpR6dyzszPAzv8EbRjeAPgivziCqglCIXm7NoInki4ixV5vzUS34ZTUPY8aGUEqnMJ9Fu5eh7T9hRyTyB9-A21JDrArOOdVtioXeDBBtYWzFw7OBC3zTUeYtQs0HKgYaOWGnB2dZZZG_xljryLfZYDyOCX5Oj6-iigjrQ9FevotXz08d8ES_fX17ns2WMKsu7mDSgUKVCk2IpyzwBk-vEZHxNWWVIDq9qIKNRSAUi45AYXUnkGqGsFIG6iu6Od7dQF3tvG_B90YItFrNlMe44NyZRSfYlBvb2yO59-3mg0BWNDUh1DY7aQyhEPsKpzpL_0UTkWvNMjej9EUXfhuCpOtkQvBijKv6iUj8Ef4ep</recordid><startdate>20130101</startdate><enddate>20130101</enddate><creator>Despagnet-Ayoub, Emmanuelle</creator><creator>Miqueu, Karinne</creator><creator>Sotiropoulos, Jean-Marc</creator><creator>Henling, Lawrence M</creator><creator>Day, Michael W</creator><creator>Labinger, Jay A</creator><creator>Bercaw, John E</creator><general>The Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0001-9513-3639</orcidid><orcidid>https://orcid.org/0000-0002-5960-1877</orcidid></search><sort><creationdate>20130101</creationdate><title>Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene</title><author>Despagnet-Ayoub, Emmanuelle ; Miqueu, Karinne ; Sotiropoulos, Jean-Marc ; Henling, Lawrence M ; Day, Michael W ; Labinger, Jay A ; Bercaw, John E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c367t-e8ac13d3c95cd2d74a9784960be6f9e21038ae98c123a160a498f2c08cadf3ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Bearing</topic><topic>Carbenes</topic><topic>Chemical Sciences</topic><topic>Coordination chemistry</topic><topic>Isomers</topic><topic>Pathways</topic><topic>Phenol</topic><topic>Precursors</topic><topic>Synthesis</topic><topic>Zirconium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Despagnet-Ayoub, Emmanuelle</creatorcontrib><creatorcontrib>Miqueu, Karinne</creatorcontrib><creatorcontrib>Sotiropoulos, Jean-Marc</creatorcontrib><creatorcontrib>Henling, Lawrence M</creatorcontrib><creatorcontrib>Day, Michael W</creatorcontrib><creatorcontrib>Labinger, Jay A</creatorcontrib><creatorcontrib>Bercaw, John E</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Despagnet-Ayoub, Emmanuelle</au><au>Miqueu, Karinne</au><au>Sotiropoulos, Jean-Marc</au><au>Henling, Lawrence M</au><au>Day, Michael W</au><au>Labinger, Jay A</au><au>Bercaw, John E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2013-01-01</date><risdate>2013</risdate><volume>4</volume><issue>5</issue><spage>2117</spage><epage>2121</epage><pages>2117-2121</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Starting from the same ethylenediamine species, three valuable carbene precursors were synthesized under differing conditions: a tridentate dianionic N-heterocyclic carbene bearing an aniline, a phenol and a central dihydroimidazolium salt, its benzimidazolium isomer by intramolecular rearrangement and a dicationic benzimidazolium-benzoxazolium salt by changing the Broensted acid from HCl to HBF sub(4). 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| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2013-01, Vol.4 (5), p.2117-2121 |
| issn | 2041-6520 2041-6539 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Bearing Carbenes Chemical Sciences Coordination chemistry Isomers Pathways Phenol Precursors Synthesis Zirconium |
| title | Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene |
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