Reaction of mono-epoxidized conjugated linoleic acid ester with boron trifluoride etherate complex
The reaction of methyl 11, 12‐E‐epoxy‐9Z‐octadecenoate (1) with boron trifluoride etherate furnished a mixture of methyl 12‐oxo‐10E‐octadecenoate (3a) and methyl 11‐oxo‐9E‐octadecenoate (3b) in 66% yield. Methyl 9, 10‐Z‐epoxy‐11 E‐octadecenoate (2) with boron trifluoride etherate furnished a mixture...
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| Veröffentlicht in: | Lipids 2004-06, Vol.39 (6), p.583-587 |
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| creator | Jie, M.S.F.L.K Lam, C.N.W |
| description | The reaction of methyl 11, 12‐E‐epoxy‐9Z‐octadecenoate (1) with boron trifluoride etherate furnished a mixture of methyl 12‐oxo‐10E‐octadecenoate (3a) and methyl 11‐oxo‐9E‐octadecenoate (3b) in 66% yield. Methyl 9, 10‐Z‐epoxy‐11 E‐octadecenoate (2) with boron trifluoride etherate furnished a mixture of methyl 9‐oxo‐10 E‐octadecenoate (4a, 45%) and methyl 10‐oxo‐11 E‐octadecenoate (4b, 19%). A plausible mechanism is proposed for these reactions, which involves the attack on the epoxy ring system by BF3, followed by deprotonation, oxo formation, and double bond migration to give a mixture of two positional α,β‐unsaturated C18 enone ester derivatives (3a/3b, 4a/4b). The structures of these C18 enone ester derivatives (3a/3b, 4a/4b) were identified by a combination of NMR spectroscopic and mass spectrometric analyses. |
| doi_str_mv | 10.1007/s11745-004-1267-6 |
| format | Article |
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Methyl 9, 10‐Z‐epoxy‐11 E‐octadecenoate (2) with boron trifluoride etherate furnished a mixture of methyl 9‐oxo‐10 E‐octadecenoate (4a, 45%) and methyl 10‐oxo‐11 E‐octadecenoate (4b, 19%). A plausible mechanism is proposed for these reactions, which involves the attack on the epoxy ring system by BF3, followed by deprotonation, oxo formation, and double bond migration to give a mixture of two positional α,β‐unsaturated C18 enone ester derivatives (3a/3b, 4a/4b). The structures of these C18 enone ester derivatives (3a/3b, 4a/4b) were identified by a combination of NMR spectroscopic and mass spectrometric analyses.</description><identifier>ISSN: 0024-4201</identifier><identifier>EISSN: 1558-9307</identifier><identifier>DOI: 10.1007/s11745-004-1267-6</identifier><identifier>PMID: 15554159</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer‐Verlag</publisher><subject>Boranes - chemistry ; Boron ; chemical reactions ; epoxidation ; Epoxy Compounds - chemistry ; Esters - chemistry ; Linoleic Acids, Conjugated - chemistry ; Molecular Structure</subject><ispartof>Lipids, 2004-06, Vol.39 (6), p.583-587</ispartof><rights>2004 American Oil Chemists' Society (AOCS)</rights><rights>Copyright AOCS Press Jun 2004</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3963-14d8bd9fbdd9da69ba855c1c8bba81561ba9ff09480b06cd4741487e3d519bd53</citedby><cites>FETCH-LOGICAL-c3963-14d8bd9fbdd9da69ba855c1c8bba81561ba9ff09480b06cd4741487e3d519bd53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1007%2Fs11745-004-1267-6$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1007%2Fs11745-004-1267-6$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15554159$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jie, M.S.F.L.K</creatorcontrib><creatorcontrib>Lam, C.N.W</creatorcontrib><title>Reaction of mono-epoxidized conjugated linoleic acid ester with boron trifluoride etherate complex</title><title>Lipids</title><addtitle>Lipids</addtitle><description>The reaction of methyl 11, 12‐E‐epoxy‐9Z‐octadecenoate (1) with boron trifluoride etherate furnished a mixture of methyl 12‐oxo‐10E‐octadecenoate (3a) and methyl 11‐oxo‐9E‐octadecenoate (3b) in 66% yield. Methyl 9, 10‐Z‐epoxy‐11 E‐octadecenoate (2) with boron trifluoride etherate furnished a mixture of methyl 9‐oxo‐10 E‐octadecenoate (4a, 45%) and methyl 10‐oxo‐11 E‐octadecenoate (4b, 19%). A plausible mechanism is proposed for these reactions, which involves the attack on the epoxy ring system by BF3, followed by deprotonation, oxo formation, and double bond migration to give a mixture of two positional α,β‐unsaturated C18 enone ester derivatives (3a/3b, 4a/4b). The structures of these C18 enone ester derivatives (3a/3b, 4a/4b) were identified by a combination of NMR spectroscopic and mass spectrometric analyses.</description><subject>Boranes - chemistry</subject><subject>Boron</subject><subject>chemical reactions</subject><subject>epoxidation</subject><subject>Epoxy Compounds - chemistry</subject><subject>Esters - chemistry</subject><subject>Linoleic Acids, Conjugated - chemistry</subject><subject>Molecular Structure</subject><issn>0024-4201</issn><issn>1558-9307</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNqFkUtv1DAURi0EokPhB7CBiAW7lHsTP-IlanlUGokK6NryK61HSTzYifr49XiUkZDYdOVr6ZxPV98l5C3CGQKITxlRUFYD0BobLmr-jGyQsa6WLYjnZAPQ0Jo2gCfkVc678kUq2UtyUiBGkckNMT-9tnOIUxX7aoxTrP0-3gcXHr2rbJx2y42eyziEKQ4-2Erb4CqfZ5-quzDfViamIs8p9MMSU3C-8vOtT0Uq-rgf_P1r8qLXQ_Zvju8puf765ff593r749vl-edtbVvJ2xqp64yTvXFOOs2l0R1jFm1nyoSMo9Gy70HSDgxw66igSDvhW8dQGsfaU_Jxzd2n-GcpK6oxZOuHQU8-LllxAUJy2RXww3_gLi5pKruphjUNAyYPabhCNsWck-_VPoVRpweFoA7tq7V9VdpXh_YVL867Y_BiRu_-Gce6CyBW4C4M_uHpRLW9vLoA1rXFfL-avY5K36SQ1fWvctkWQHJAlO1fNaeapw</recordid><startdate>200406</startdate><enddate>200406</enddate><creator>Jie, M.S.F.L.K</creator><creator>Lam, C.N.W</creator><general>Springer‐Verlag</general><general>Springer Nature B.V</general><scope>FBQ</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7QL</scope><scope>7QP</scope><scope>7QR</scope><scope>7T7</scope><scope>7TK</scope><scope>7U9</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PCBAR</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>7X8</scope></search><sort><creationdate>200406</creationdate><title>Reaction of mono-epoxidized conjugated linoleic acid ester with boron trifluoride etherate complex</title><author>Jie, M.S.F.L.K ; 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Methyl 9, 10‐Z‐epoxy‐11 E‐octadecenoate (2) with boron trifluoride etherate furnished a mixture of methyl 9‐oxo‐10 E‐octadecenoate (4a, 45%) and methyl 10‐oxo‐11 E‐octadecenoate (4b, 19%). A plausible mechanism is proposed for these reactions, which involves the attack on the epoxy ring system by BF3, followed by deprotonation, oxo formation, and double bond migration to give a mixture of two positional α,β‐unsaturated C18 enone ester derivatives (3a/3b, 4a/4b). The structures of these C18 enone ester derivatives (3a/3b, 4a/4b) were identified by a combination of NMR spectroscopic and mass spectrometric analyses.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer‐Verlag</pub><pmid>15554159</pmid><doi>10.1007/s11745-004-1267-6</doi><tpages>5</tpages></addata></record> |
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| source | MEDLINE; Springer Nature - Complete Springer Journals; Wiley Online Library Journals Frontfile Complete |
| subjects | Boranes - chemistry Boron chemical reactions epoxidation Epoxy Compounds - chemistry Esters - chemistry Linoleic Acids, Conjugated - chemistry Molecular Structure |
| title | Reaction of mono-epoxidized conjugated linoleic acid ester with boron trifluoride etherate complex |
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